NPASS Compound

Structure

NPC470704 OpenBabel07101719522D 25 28 0 0 0 0 0 0 0 0999 V2000 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 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 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 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 1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.8271 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 -2.6831 0.3090 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 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 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 -6.1472 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 3.5497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 7 2 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.06
Volume:	323.462
LogP:	3.493
LogD:	2.387
LogS:	-3.681
# Rotatable Bonds:	1
TPSA:	134.52
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.231
Synthetic Accessibility Score:	2.719
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.752
MDCK Permeability:	5.494404376804596e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.377
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.73381805419922%
Volume Distribution (VD):	0.495
Pgp-substrate:	7.456356048583984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.636
CYP2C9-substrate:	0.582
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	11.304
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.703
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.305
Skin Sensitization:	0.941
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.914
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC470704

Natural Product ID:	NPC470704
*Common Name:**	Cycloleucomelone
IUPAC Name:	3-(4-hydroxyphenyl)dibenzofuran-1,2,4,7,8-pentol
Synonyms:	Cycloleucomelone
Standard InCHIKey:	KPLKPGSATMNRTH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O7/c19-8-3-1-7(2-4-8)13-15(22)16(23)14-9-5-10(20)11(21)6-12(9)25-18(14)17(13)24/h1-6,19-24H
SMILES:	Oc1ccc(cc1)c1c(O)c(O)c2c(c1O)oc1c2cc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL219810
PubChem CID:	10065824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0002584] Phenylbenzofurans

*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
NPO22584	Thelephora vialis	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16901696]
NPO22584	Thelephora vialis	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22584	Thelephora vialis	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22584	Thelephora vialis	Species	Thelephoraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	3500.0	nM	PMID[468685]

☑ 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 NPC470704 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	603
0.1-0.2	2321
0.2-0.3	5373
0.3-0.4	11870
0.4-0.5	5061
0.5-0.6	4203
0.6-0.7	5392
0.7-0.8	5245
0.8-0.85	1540
0.85-0.9	812
0.9-0.95	263
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC54098
0.9812	High Similarity	NPC230619
0.9752	High Similarity	NPC216842
0.9752	High Similarity	NPC82217
0.9752	High Similarity	NPC476640
0.9691	High Similarity	NPC287243
0.9632	High Similarity	NPC49667
0.9632	High Similarity	NPC8127
0.9627	High Similarity	NPC476641
0.9573	High Similarity	NPC98546
0.9573	High Similarity	NPC297807
0.9509	High Similarity	NPC65885
0.9458	High Similarity	NPC47883
0.9437	High Similarity	NPC263092
0.9437	High Similarity	NPC39305
0.9437	High Similarity	NPC59295
0.9437	High Similarity	NPC1755
0.9437	High Similarity	NPC1706
0.9434	High Similarity	NPC188486
0.9427	High Similarity	NPC472461
0.9379	High Similarity	NPC45449
0.9379	High Similarity	NPC36320
0.9375	High Similarity	NPC312056
0.9375	High Similarity	NPC238995
0.9375	High Similarity	NPC84515
0.9345	High Similarity	NPC154527
0.9329	High Similarity	NPC174700
0.9325	High Similarity	NPC202470
0.9308	High Similarity	NPC16935
0.9308	High Similarity	NPC196879
0.929	High Similarity	NPC226725
0.9277	High Similarity	NPC471841
0.9273	High Similarity	NPC473834
0.9273	High Similarity	NPC149846
0.9264	High Similarity	NPC50394
0.9255	High Similarity	NPC272722
0.9236	High Similarity	NPC125300
0.9235	High Similarity	NPC248315
0.9198	High Similarity	NPC133065
0.9182	High Similarity	NPC45131
0.9157	High Similarity	NPC117450
0.9146	High Similarity	NPC247973
0.9141	High Similarity	NPC39306
0.9141	High Similarity	NPC29411
0.9118	High Similarity	NPC71260
0.9107	High Similarity	NPC77179
0.9107	High Similarity	NPC23553
0.9102	High Similarity	NPC227906
0.9096	High Similarity	NPC248593
0.9096	High Similarity	NPC28589
0.9091	High Similarity	NPC247136
0.9085	High Similarity	NPC277480
0.9068	High Similarity	NPC195832
0.9062	High Similarity	NPC137100
0.9059	High Similarity	NPC240508
0.9059	High Similarity	NPC471842
0.9051	High Similarity	NPC225731
0.9051	High Similarity	NPC251110
0.9042	High Similarity	NPC310794
0.9024	High Similarity	NPC37183
0.9006	High Similarity	NPC185526
0.9	High Similarity	NPC26227
0.9	High Similarity	NPC201451
0.9	High Similarity	NPC44079
0.8994	High Similarity	NPC27208
0.8994	High Similarity	NPC221820
0.8987	High Similarity	NPC260582
0.8987	High Similarity	NPC248102
0.8987	High Similarity	NPC45873
0.8987	High Similarity	NPC61620
0.897	High Similarity	NPC272560
0.8966	High Similarity	NPC60848
0.8957	High Similarity	NPC308992
0.8951	High Similarity	NPC472877
0.8951	High Similarity	NPC55738
0.8947	High Similarity	NPC246153
0.8947	High Similarity	NPC228209
0.8944	High Similarity	NPC49824
0.8944	High Similarity	NPC474638
0.8944	High Similarity	NPC266960
0.8944	High Similarity	NPC247017
0.8944	High Similarity	NPC245546
0.8944	High Similarity	NPC43243
0.8944	High Similarity	NPC98661
0.8938	High Similarity	NPC292214
0.8938	High Similarity	NPC271779
0.8938	High Similarity	NPC206238
0.8938	High Similarity	NPC167091
0.8938	High Similarity	NPC88645
0.8924	High Similarity	NPC296197
0.8924	High Similarity	NPC259713
0.8924	High Similarity	NPC216318
0.8924	High Similarity	NPC195351
0.8924	High Similarity	NPC17286
0.8922	High Similarity	NPC131866
0.8922	High Similarity	NPC28042
0.8916	High Similarity	NPC241820
0.8916	High Similarity	NPC86477
0.8909	High Similarity	NPC291110
0.8902	High Similarity	NPC294965
0.8896	High Similarity	NPC263449
0.8889	High Similarity	NPC101830
0.8889	High Similarity	NPC287979
0.8889	High Similarity	NPC305663
0.8889	High Similarity	NPC110070
0.8889	High Similarity	NPC189179
0.8889	High Similarity	NPC224137
0.8889	High Similarity	NPC75215
0.8889	High Similarity	NPC210084
0.8889	High Similarity	NPC99597
0.8889	High Similarity	NPC176665
0.8889	High Similarity	NPC163524
0.8889	High Similarity	NPC227192
0.8889	High Similarity	NPC203891
0.8889	High Similarity	NPC93376
0.8882	High Similarity	NPC20830
0.8882	High Similarity	NPC256612
0.8882	High Similarity	NPC475783
0.8882	High Similarity	NPC2928
0.8875	High Similarity	NPC241498
0.8875	High Similarity	NPC120163
0.8875	High Similarity	NPC75069
0.8875	High Similarity	NPC101996
0.8875	High Similarity	NPC83508
0.8875	High Similarity	NPC100887
0.8875	High Similarity	NPC301323
0.8875	High Similarity	NPC57030
0.8875	High Similarity	NPC304954
0.8875	High Similarity	NPC212678
0.8875	High Similarity	NPC180234
0.8875	High Similarity	NPC199100
0.8875	High Similarity	NPC131624
0.8875	High Similarity	NPC120537
0.8875	High Similarity	NPC25270
0.8875	High Similarity	NPC239128
0.8875	High Similarity	NPC161277
0.8875	High Similarity	NPC293183
0.8875	High Similarity	NPC256283
0.8875	High Similarity	NPC275836
0.8875	High Similarity	NPC301123
0.8875	High Similarity	NPC55205
0.8875	High Similarity	NPC187498
0.8875	High Similarity	NPC162313
0.8875	High Similarity	NPC71334
0.8875	High Similarity	NPC188203
0.8875	High Similarity	NPC198826
0.8875	High Similarity	NPC222830
0.8875	High Similarity	NPC275722
0.8875	High Similarity	NPC156222
0.8875	High Similarity	NPC39007
0.8868	High Similarity	NPC77858
0.8868	High Similarity	NPC167576
0.8861	High Similarity	NPC43669
0.8861	High Similarity	NPC194856
0.8861	High Similarity	NPC272721
0.8861	High Similarity	NPC118726
0.8861	High Similarity	NPC196277
0.8861	High Similarity	NPC12367
0.8861	High Similarity	NPC276930
0.8861	High Similarity	NPC19545
0.8848	High Similarity	NPC270837
0.8848	High Similarity	NPC110257
0.8841	High Similarity	NPC231758
0.8841	High Similarity	NPC34089
0.8841	High Similarity	NPC311740
0.8841	High Similarity	NPC196179
0.8841	High Similarity	NPC162668
0.8837	High Similarity	NPC8927
0.8834	High Similarity	NPC193842
0.8834	High Similarity	NPC152166
0.8834	High Similarity	NPC9609
0.8834	High Similarity	NPC18607
0.8834	High Similarity	NPC7846
0.8834	High Similarity	NPC154304
0.8834	High Similarity	NPC25495
0.8834	High Similarity	NPC143828
0.8834	High Similarity	NPC190487
0.8834	High Similarity	NPC130894
0.8834	High Similarity	NPC176300
0.8834	High Similarity	NPC300943
0.8834	High Similarity	NPC253634
0.8834	High Similarity	NPC19687
0.8834	High Similarity	NPC152904
0.8834	High Similarity	NPC261004
0.8834	High Similarity	NPC105242
0.8834	High Similarity	NPC288669
0.8834	High Similarity	NPC115798
0.8834	High Similarity	NPC191459
0.8834	High Similarity	NPC22472
0.8834	High Similarity	NPC18772
0.8834	High Similarity	NPC4481
0.8834	High Similarity	NPC204854
0.883	High Similarity	NPC476273
0.8827	High Similarity	NPC201837
0.8827	High Similarity	NPC265511
0.8827	High Similarity	NPC235165
0.8827	High Similarity	NPC255106
0.8827	High Similarity	NPC138243
0.8827	High Similarity	NPC191146
0.8827	High Similarity	NPC274730

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 NPC470704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	499
0.1-0.2	1078
0.2-0.3	1919
0.3-0.4	2774
0.4-0.5	1588
0.5-0.6	878
0.6-0.7	273
0.7-0.8	112
0.8-0.85	15
0.85-0.9	9
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8827	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD2801	Approved
0.8734	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD1934	Approved
0.8608	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD3818	Discontinued
0.8434	Intermediate Similarity	NPD3749	Approved
0.8402	Intermediate Similarity	NPD3926	Phase 2
0.8393	Intermediate Similarity	NPD1247	Approved
0.8364	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD5494	Approved
0.8304	Intermediate Similarity	NPD7473	Discontinued
0.8263	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8204	Intermediate Similarity	NPD3817	Phase 2
0.8144	Intermediate Similarity	NPD1465	Phase 2
0.8114	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6559	Discontinued
0.8059	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD2344	Approved
0.7965	Intermediate Similarity	NPD6959	Discontinued
0.7964	Intermediate Similarity	NPD6599	Discontinued
0.7962	Intermediate Similarity	NPD943	Approved
0.7955	Intermediate Similarity	NPD7074	Phase 3
0.795	Intermediate Similarity	NPD1549	Phase 2
0.791	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD7054	Approved
0.7895	Intermediate Similarity	NPD7075	Discontinued
0.7888	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5402	Approved
0.7879	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1510	Phase 2
0.7865	Intermediate Similarity	NPD7251	Discontinued
0.7862	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7472	Approved
0.7824	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7808	Phase 3
0.7818	Intermediate Similarity	NPD6799	Approved
0.7805	Intermediate Similarity	NPD2309	Approved
0.7791	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1240	Approved
0.7683	Intermediate Similarity	NPD2800	Approved
0.7679	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6801	Discontinued
0.764	Intermediate Similarity	NPD3751	Discontinued
0.7636	Intermediate Similarity	NPD3750	Approved
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7627	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7819	Suspended
0.7607	Intermediate Similarity	NPD2796	Approved
0.7602	Intermediate Similarity	NPD7411	Suspended
0.7596	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD1243	Approved
0.7574	Intermediate Similarity	NPD920	Approved
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2532	Approved
0.756	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2533	Approved
0.756	Intermediate Similarity	NPD2534	Approved
0.7546	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7487	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4287	Approved
0.7471	Intermediate Similarity	NPD5403	Approved
0.7469	Intermediate Similarity	NPD447	Suspended
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7458	Intermediate Similarity	NPD7199	Phase 2
0.7456	Intermediate Similarity	NPD5401	Approved
0.7443	Intermediate Similarity	NPD6234	Discontinued
0.744	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3787	Discontinued
0.741	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1613	Approved
0.7396	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7381	Intermediate Similarity	NPD6190	Approved
0.7362	Intermediate Similarity	NPD230	Phase 1
0.7349	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD2346	Discontinued
0.7333	Intermediate Similarity	NPD3748	Approved
0.7321	Intermediate Similarity	NPD4628	Phase 3
0.7297	Intermediate Similarity	NPD8312	Approved
0.7297	Intermediate Similarity	NPD8313	Approved
0.7289	Intermediate Similarity	NPD6099	Approved
0.7289	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD2296	Approved
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD37	Approved
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4967	Phase 2
0.7232	Intermediate Similarity	NPD4965	Approved
0.7232	Intermediate Similarity	NPD4966	Approved
0.7216	Intermediate Similarity	NPD6780	Approved
0.7216	Intermediate Similarity	NPD6777	Approved
0.7216	Intermediate Similarity	NPD6776	Approved
0.7216	Intermediate Similarity	NPD6781	Approved
0.7216	Intermediate Similarity	NPD6779	Approved
0.7216	Intermediate Similarity	NPD6782	Approved
0.7216	Intermediate Similarity	NPD6778	Approved
0.7186	Intermediate Similarity	NPD5408	Approved
0.7186	Intermediate Similarity	NPD5404	Approved
0.7186	Intermediate Similarity	NPD5406	Approved
0.7186	Intermediate Similarity	NPD5405	Approved
0.7178	Intermediate Similarity	NPD3764	Approved
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7158	Intermediate Similarity	NPD7228	Approved
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1653	Approved
0.7126	Intermediate Similarity	NPD2799	Discontinued
0.7118	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3027	Phase 3
0.7107	Intermediate Similarity	NPD7435	Discontinued
0.7099	Intermediate Similarity	NPD9494	Approved
0.709	Intermediate Similarity	NPD8150	Discontinued
0.7081	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD1470	Approved
0.7071	Intermediate Similarity	NPD7870	Phase 2
0.7071	Intermediate Similarity	NPD7871	Phase 2
0.7059	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2403	Approved
0.7048	Intermediate Similarity	NPD1933	Approved
0.7041	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4111	Phase 1
0.7039	Intermediate Similarity	NPD4665	Approved
0.7033	Intermediate Similarity	NPD5711	Approved
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD5710	Approved
0.702	Intermediate Similarity	NPD7696	Phase 3
0.702	Intermediate Similarity	NPD7697	Approved
0.702	Intermediate Similarity	NPD7698	Approved
0.7018	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6989	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD2163	Approved
0.6973	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7907	Approved
0.697	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7701	Phase 2
0.6959	Remote Similarity	NPD6534	Approved
0.6959	Remote Similarity	NPD6535	Approved
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5953	Discontinued
0.6951	Remote Similarity	NPD4908	Phase 1
0.6946	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7783	Phase 2
0.6937	Remote Similarity	NPD1201	Approved
0.6935	Remote Similarity	NPD7286	Phase 2
0.6928	Remote Similarity	NPD6233	Phase 2
0.6927	Remote Similarity	NPD5761	Phase 2
0.6927	Remote Similarity	NPD5760	Phase 2
0.6923	Remote Similarity	NPD4308	Phase 3
0.6915	Remote Similarity	NPD7685	Pre-registration
0.6909	Remote Similarity	NPD4625	Phase 3
0.6902	Remote Similarity	NPD5242	Approved
0.6897	Remote Similarity	NPD7874	Approved
0.6897	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6280	Approved
0.6872	Remote Similarity	NPD6279	Approved
0.6867	Remote Similarity	NPD6798	Discontinued
0.6867	Remote Similarity	NPD411	Approved
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7801	Approved
0.6853	Remote Similarity	NPD7700	Phase 2
0.6853	Remote Similarity	NPD7699	Phase 2
0.6834	Remote Similarity	NPD3452	Approved
0.6834	Remote Similarity	NPD3450	Approved
0.6834	Remote Similarity	NPD2493	Approved
0.6834	Remote Similarity	NPD2494	Approved
0.6832	Remote Similarity	NPD1610	Phase 2
0.6832	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2798	Approved
0.6805	Remote Similarity	NPD6651	Approved
0.68	Remote Similarity	NPD6823	Phase 2
0.6798	Remote Similarity	NPD7458	Discontinued
0.6796	Remote Similarity	NPD4288	Approved
0.6791	Remote Similarity	NPD7177	Discontinued
0.679	Remote Similarity	NPD1608	Approved
0.679	Remote Similarity	NPD9717	Approved
0.6789	Remote Similarity	NPD7549	Discontinued

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