NPASS Compound

Structure

NPC248315 OpenBabel07101718282D 38 42 0 0 0 0 0 0 0 0999 V2000 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3979 -4.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5844 -6.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4034 -4.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5790 -6.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9857 -5.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9967 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1668 -7.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9802 -5.2691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1613 -6.9917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7600 -8.0097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0021 -5.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 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 20 1 0 0 0 0 4 21 1 0 0 0 0 5 11 2 0 0 0 0 5 18 1 0 0 0 0 6 12 2 0 0 0 0 6 19 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 17 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 17 1 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 29 1 0 0 0 0 20 35 1 0 0 0 0 21 37 1 0 0 0 0 22 36 1 0 0 0 0 23 24 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 30 2 0 0 0 0 25 31 1 0 0 0 0 32 38 1 0 0 0 0 33 38 2 0 0 0 0 34 38 2 0 0 0 0 37 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.04
Volume:	487.892
LogP:	4.144
LogD:	2.09
LogS:	-3.221
# Rotatable Bonds:	6
TPSA:	204.19
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.161
Synthetic Accessibility Score:	2.978
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097
MDCK Permeability:	8.021275789360516e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.62
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	99.40904998779297%
Volume Distribution (VD):	0.265
Pgp-substrate:	0.7296844720840454%

ADMET: Metabolism

CYP1A2-inhibitor:	0.626
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.932
Half-life (T1/2):	0.59

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.888
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.289
Carcinogencity:	0.796
Eye Corrosion:	0.003
Eye Irritation:	0.632
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC248315

Natural Product ID:	NPC248315
*Common Name:**	6-(3,3'-Dihydroxy-4'-Sulfooxy-Biphenyl-4-Yloxy)-2,8-Dihydroxy-Dibenzofuran-3-Carboxylic Acid
IUPAC Name:	2,8-dihydroxy-6-[2-hydroxy-4-(3-hydroxy-4-sulfooxyphenyl)phenoxy]dibenzofuran-3-carboxylic acid
Synonyms:
Standard InCHIKey:	FRUOIAVWHGWBQO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H16O12S/c26-13-7-15-14-9-17(27)16(25(30)31)10-22(14)36-24(15)23(8-13)35-20-3-1-11(5-18(20)28)12-2-4-21(19(29)6-12)37-38(32,33)34/h1-10,26-29H,(H,30,31)(H,32,33,34)
SMILES:	c1cc(c(cc1c1ccc(c(c1)O)OS(=O)(=O)O)O)Oc1cc(cc2c3cc(c(cc3oc12)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251431
PubChem CID:	24178901
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	=	1700.0	nM	PMID[559970]

☑ 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 NPC248315 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	575
0.1-0.2	2433
0.2-0.3	5782
0.3-0.4	11415
0.4-0.5	5568
0.5-0.6	4485
0.6-0.7	5898
0.7-0.8	4912
0.8-0.85	1369
0.85-0.9	240
0.9-0.95	18
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC47883
0.9483	High Similarity	NPC226725
0.9425	High Similarity	NPC154527
0.9419	High Similarity	NPC98546
0.9419	High Similarity	NPC297807
0.9244	High Similarity	NPC476640
0.9244	High Similarity	NPC82217
0.9244	High Similarity	NPC216842
0.9235	High Similarity	NPC470704
0.9191	High Similarity	NPC287243
0.9186	High Similarity	NPC230619
0.9186	High Similarity	NPC54098
0.9138	High Similarity	NPC49667
0.9138	High Similarity	NPC8127
0.9133	High Similarity	NPC149846
0.9128	High Similarity	NPC476641
0.9096	High Similarity	NPC71260
0.9023	High Similarity	NPC65885
0.9	High Similarity	NPC295436
0.8966	High Similarity	NPC174700
0.892	High Similarity	NPC471841
0.8914	High Similarity	NPC473834
0.8895	High Similarity	NPC29411
0.8895	High Similarity	NPC36320
0.8895	High Similarity	NPC45449
0.8876	High Similarity	NPC475996
0.8851	High Similarity	NPC280493
0.8851	High Similarity	NPC202470
0.8837	High Similarity	NPC1706
0.8837	High Similarity	NPC59295
0.8837	High Similarity	NPC39305
0.8837	High Similarity	NPC263092
0.8837	High Similarity	NPC1755
0.8814	High Similarity	NPC24258
0.8807	High Similarity	NPC117450
0.8779	High Similarity	NPC312056
0.8779	High Similarity	NPC272722
0.8779	High Similarity	NPC238995
0.8779	High Similarity	NPC84515
0.8765	High Similarity	NPC185526
0.875	High Similarity	NPC476370
0.875	High Similarity	NPC247964
0.8743	High Similarity	NPC476279
0.8722	High Similarity	NPC471842
0.8721	High Similarity	NPC231758
0.8721	High Similarity	NPC188486
0.8706	High Similarity	NPC472461
0.8706	High Similarity	NPC137100
0.8701	High Similarity	NPC476374
0.8701	High Similarity	NPC261471
0.8693	High Similarity	NPC218533
0.8693	High Similarity	NPC78830
0.8693	High Similarity	NPC72696
0.8686	High Similarity	NPC86477
0.8686	High Similarity	NPC50394
0.8659	High Similarity	NPC475783
0.8644	High Similarity	NPC158226
0.8636	High Similarity	NPC247136
0.8629	High Similarity	NPC272560
0.8621	High Similarity	NPC133065
0.8621	High Similarity	NPC89131
0.8613	High Similarity	NPC34089
0.8613	High Similarity	NPC196179
0.8605	High Similarity	NPC190487
0.8605	High Similarity	NPC195832
0.8605	High Similarity	NPC196879
0.8605	High Similarity	NPC154304
0.8605	High Similarity	NPC16935
0.8603	High Similarity	NPC164384
0.8596	High Similarity	NPC310794
0.8596	High Similarity	NPC37606
0.858	High Similarity	NPC247973
0.8579	High Similarity	NPC269625
0.8579	High Similarity	NPC174486
0.8571	High Similarity	NPC39306
0.8571	High Similarity	NPC259757
0.8564	High Similarity	NPC222674
0.8556	High Similarity	NPC23553
0.8556	High Similarity	NPC77179
0.8555	High Similarity	NPC188967
0.8555	High Similarity	NPC300680
0.8555	High Similarity	NPC130955
0.8547	High Similarity	NPC99591
0.8547	High Similarity	NPC227906
0.8539	High Similarity	NPC28589
0.8539	High Similarity	NPC248593
0.8531	High Similarity	NPC99613
0.8531	High Similarity	NPC165979
0.8531	High Similarity	NPC163130
0.8531	High Similarity	NPC49487
0.8529	High Similarity	NPC125300
0.8523	High Similarity	NPC277480
0.8516	High Similarity	NPC240508
0.8516	High Similarity	NPC107987
0.8514	High Similarity	NPC272064
0.8508	High Similarity	NPC476273
0.85	High Similarity	NPC296018
0.85	High Similarity	NPC154741
0.8497	Intermediate Similarity	NPC176300
0.8497	Intermediate Similarity	NPC253634
0.8497	Intermediate Similarity	NPC19687
0.8497	Intermediate Similarity	NPC115798
0.8497	Intermediate Similarity	NPC204854
0.8497	Intermediate Similarity	NPC193842
0.8497	Intermediate Similarity	NPC22472
0.8497	Intermediate Similarity	NPC152166
0.8497	Intermediate Similarity	NPC9609
0.8497	Intermediate Similarity	NPC7846
0.8497	Intermediate Similarity	NPC18772
0.8497	Intermediate Similarity	NPC4481
0.8497	Intermediate Similarity	NPC143828
0.8497	Intermediate Similarity	NPC130894
0.8497	Intermediate Similarity	NPC105242
0.8497	Intermediate Similarity	NPC25495
0.8497	Intermediate Similarity	NPC300943
0.8497	Intermediate Similarity	NPC18607
0.8497	Intermediate Similarity	NPC261004
0.8497	Intermediate Similarity	NPC288669
0.8497	Intermediate Similarity	NPC191459
0.8492	Intermediate Similarity	NPC233956
0.8488	Intermediate Similarity	NPC45131
0.8483	Intermediate Similarity	NPC28042
0.8483	Intermediate Similarity	NPC476365
0.8478	Intermediate Similarity	NPC47905
0.8478	Intermediate Similarity	NPC139683
0.8478	Intermediate Similarity	NPC73929
0.8475	Intermediate Similarity	NPC76482
0.8475	Intermediate Similarity	NPC234331
0.847	Intermediate Similarity	NPC476170
0.8466	Intermediate Similarity	NPC169471
0.8466	Intermediate Similarity	NPC37183
0.8466	Intermediate Similarity	NPC280893
0.8466	Intermediate Similarity	NPC291110
0.8462	Intermediate Similarity	NPC97523
0.8453	Intermediate Similarity	NPC221820
0.8453	Intermediate Similarity	NPC476773
0.8453	Intermediate Similarity	NPC246877
0.8444	Intermediate Similarity	NPC289244
0.8444	Intermediate Similarity	NPC245975
0.8441	Intermediate Similarity	NPC60848
0.8439	Intermediate Similarity	NPC176665
0.8439	Intermediate Similarity	NPC112954
0.8439	Intermediate Similarity	NPC189179
0.8439	Intermediate Similarity	NPC93376
0.8439	Intermediate Similarity	NPC224137
0.8439	Intermediate Similarity	NPC163524
0.8439	Intermediate Similarity	NPC78302
0.8439	Intermediate Similarity	NPC110070
0.8439	Intermediate Similarity	NPC227192
0.8439	Intermediate Similarity	NPC203891
0.8439	Intermediate Similarity	NPC472438
0.8439	Intermediate Similarity	NPC101830
0.8439	Intermediate Similarity	NPC7973
0.8439	Intermediate Similarity	NPC75215
0.8439	Intermediate Similarity	NPC29841
0.8439	Intermediate Similarity	NPC287979
0.8439	Intermediate Similarity	NPC305663
0.8439	Intermediate Similarity	NPC174908
0.8439	Intermediate Similarity	NPC235215
0.8436	Intermediate Similarity	NPC271848
0.8436	Intermediate Similarity	NPC81332
0.8436	Intermediate Similarity	NPC262580
0.8436	Intermediate Similarity	NPC289396
0.8436	Intermediate Similarity	NPC212038
0.8436	Intermediate Similarity	NPC47386
0.843	Intermediate Similarity	NPC80489
0.843	Intermediate Similarity	NPC292385
0.843	Intermediate Similarity	NPC125709
0.8427	Intermediate Similarity	NPC216403
0.8427	Intermediate Similarity	NPC186100
0.8427	Intermediate Similarity	NPC41494
0.8424	Intermediate Similarity	NPC304322
0.8421	Intermediate Similarity	NPC27208
0.8418	Intermediate Similarity	NPC29160
0.8415	Intermediate Similarity	NPC36138
0.8415	Intermediate Similarity	NPC246153
0.8415	Intermediate Similarity	NPC228209
0.8412	Intermediate Similarity	NPC260582
0.8409	Intermediate Similarity	NPC67959
0.84	Intermediate Similarity	NPC112418
0.8398	Intermediate Similarity	NPC156955
0.8398	Intermediate Similarity	NPC107244
0.8398	Intermediate Similarity	NPC268533
0.8398	Intermediate Similarity	NPC216307
0.8391	Intermediate Similarity	NPC287458
0.8391	Intermediate Similarity	NPC472877
0.8391	Intermediate Similarity	NPC36354
0.8389	Intermediate Similarity	NPC30550
0.8382	Intermediate Similarity	NPC474520
0.8382	Intermediate Similarity	NPC266960
0.8382	Intermediate Similarity	NPC292107
0.8382	Intermediate Similarity	NPC200388
0.8382	Intermediate Similarity	NPC247017
0.8382	Intermediate Similarity	NPC55619
0.8382	Intermediate Similarity	NPC245546
0.8382	Intermediate Similarity	NPC178854
0.8382	Intermediate Similarity	NPC49824
0.8382	Intermediate Similarity	NPC98661
0.8382	Intermediate Similarity	NPC268161
0.8382	Intermediate Similarity	NPC265511

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 NPC248315 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	2157
0.3-0.4	2755
0.4-0.5	1593
0.5-0.6	732
0.6-0.7	233
0.7-0.8	96
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8382	Intermediate Similarity	NPD3882	Suspended
0.8352	Intermediate Similarity	NPD6232	Discontinued
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD7473	Discontinued
0.8276	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD2801	Approved
0.8258	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6166	Phase 2
0.8232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD3749	Approved
0.8218	Intermediate Similarity	NPD3817	Phase 2
0.8167	Intermediate Similarity	NPD3818	Discontinued
0.8122	Intermediate Similarity	NPD5844	Phase 1
0.8101	Intermediate Similarity	NPD3926	Phase 2
0.807	Intermediate Similarity	NPD1512	Approved
0.8057	Intermediate Similarity	NPD1465	Phase 2
0.8011	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD1934	Approved
0.7979	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD1511	Approved
0.7933	Intermediate Similarity	NPD5494	Approved
0.7921	Intermediate Similarity	NPD7075	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7889	Intermediate Similarity	NPD1247	Approved
0.7886	Intermediate Similarity	NPD6599	Discontinued
0.7877	Intermediate Similarity	NPD919	Approved
0.7853	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6797	Phase 2
0.7801	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD7251	Discontinued
0.779	Intermediate Similarity	NPD6959	Discontinued
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.776	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7808	Phase 3
0.7753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6799	Approved
0.773	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD6801	Discontinued
0.7688	Intermediate Similarity	NPD7472	Approved
0.7667	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD7411	Suspended
0.7632	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5403	Approved
0.7614	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4380	Phase 2
0.7556	Intermediate Similarity	NPD7819	Suspended
0.7528	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD5401	Approved
0.7487	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD3750	Approved
0.7447	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD8313	Approved
0.7435	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD6190	Approved
0.7418	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7435	Discontinued
0.7405	Intermediate Similarity	NPD7199	Phase 2
0.7401	Intermediate Similarity	NPD2534	Approved
0.7401	Intermediate Similarity	NPD2533	Approved
0.7401	Intermediate Similarity	NPD2532	Approved
0.7391	Intermediate Similarity	NPD6234	Discontinued
0.7366	Intermediate Similarity	NPD3787	Discontinued
0.7356	Intermediate Similarity	NPD1549	Phase 2
0.7353	Intermediate Similarity	NPD943	Approved
0.7345	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD4287	Approved
0.733	Intermediate Similarity	NPD2309	Approved
0.7318	Intermediate Similarity	NPD920	Approved
0.7314	Intermediate Similarity	NPD1243	Approved
0.7303	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1510	Phase 2
0.7267	Intermediate Similarity	NPD1607	Approved
0.7264	Intermediate Similarity	NPD6777	Approved
0.7264	Intermediate Similarity	NPD6781	Approved
0.7264	Intermediate Similarity	NPD6779	Approved
0.7264	Intermediate Similarity	NPD6776	Approved
0.7264	Intermediate Similarity	NPD6778	Approved
0.7264	Intermediate Similarity	NPD6780	Approved
0.7264	Intermediate Similarity	NPD6782	Approved
0.7247	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5404	Approved
0.7241	Intermediate Similarity	NPD2935	Discontinued
0.7241	Intermediate Similarity	NPD5406	Approved
0.7241	Intermediate Similarity	NPD5408	Approved
0.7241	Intermediate Similarity	NPD5405	Approved
0.7241	Intermediate Similarity	NPD1551	Phase 2
0.7233	Intermediate Similarity	NPD8151	Discontinued
0.7213	Intermediate Similarity	NPD37	Approved
0.7211	Intermediate Similarity	NPD7228	Approved
0.7209	Intermediate Similarity	NPD447	Suspended
0.7207	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7874	Approved
0.7198	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4966	Approved
0.7189	Intermediate Similarity	NPD4967	Phase 2
0.7189	Intermediate Similarity	NPD4965	Approved
0.7188	Intermediate Similarity	NPD5953	Discontinued
0.7184	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3748	Approved
0.7175	Intermediate Similarity	NPD4628	Phase 3
0.7159	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7122	Intermediate Similarity	NPD7871	Phase 2
0.7122	Intermediate Similarity	NPD7870	Phase 2
0.7119	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2800	Approved
0.7111	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD230	Phase 1
0.7102	Intermediate Similarity	NPD2346	Discontinued
0.709	Intermediate Similarity	NPD7229	Phase 3
0.7088	Intermediate Similarity	NPD1653	Approved
0.7086	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7697	Approved
0.7073	Intermediate Similarity	NPD7698	Approved
0.7073	Intermediate Similarity	NPD7696	Phase 3
0.7019	Intermediate Similarity	NPD7701	Phase 2
0.7018	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6535	Approved
0.7015	Intermediate Similarity	NPD6534	Approved
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7783	Phase 2
0.6989	Remote Similarity	NPD2799	Discontinued
0.6983	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7685	Pre-registration
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3764	Approved
0.6936	Remote Similarity	NPD2313	Discontinued
0.6919	Remote Similarity	NPD7801	Approved
0.6912	Remote Similarity	NPD7700	Phase 2
0.6912	Remote Similarity	NPD7699	Phase 2
0.6911	Remote Similarity	NPD5710	Approved
0.6911	Remote Similarity	NPD5711	Approved
0.691	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7286	Phase 2
0.6898	Remote Similarity	NPD8455	Phase 2
0.6897	Remote Similarity	NPD6233	Phase 2
0.6889	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8319	Approved
0.6875	Remote Similarity	NPD8320	Phase 1
0.6866	Remote Similarity	NPD7907	Approved
0.6865	Remote Similarity	NPD7458	Discontinued
0.6862	Remote Similarity	NPD2296	Approved
0.6859	Remote Similarity	NPD8127	Discontinued
0.6857	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1613	Approved
0.6856	Remote Similarity	NPD7177	Discontinued
0.6854	Remote Similarity	NPD6100	Approved
0.6854	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1203	Approved
0.6842	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6798	Discontinued
0.6839	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1933	Approved
0.6802	Remote Similarity	NPD7240	Approved
0.6796	Remote Similarity	NPD7003	Approved
0.6788	Remote Similarity	NPD5242	Approved
0.6779	Remote Similarity	NPD6823	Phase 2
0.6774	Remote Similarity	NPD4665	Approved
0.6774	Remote Similarity	NPD4111	Phase 1
0.6768	Remote Similarity	NPD7549	Discontinued
0.6765	Remote Similarity	NPD9269	Phase 2
0.6753	Remote Similarity	NPD2403	Approved
0.6746	Remote Similarity	NPD7680	Approved
0.6736	Remote Similarity	NPD6808	Phase 2
0.6727	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6355	Discontinued
0.6704	Remote Similarity	NPD4308	Phase 3
0.6686	Remote Similarity	NPD3027	Phase 3
0.6686	Remote Similarity	NPD7095	Approved
0.6684	Remote Similarity	NPD4288	Approved
0.6684	Remote Similarity	NPD2163	Approved
0.6683	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2354	Approved
0.6651	Remote Similarity	NPD2494	Approved
0.6651	Remote Similarity	NPD3452	Approved
0.6651	Remote Similarity	NPD2493	Approved
0.6651	Remote Similarity	NPD3450	Approved
0.6648	Remote Similarity	NPD3268	Approved
0.6648	Remote Similarity	NPD411	Approved
0.6647	Remote Similarity	NPD1470	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