NPASS Compound

Structure

CID159508 OpenBabel06191715532D 33 38 0 0 1 0 0 0 0 0999 V2000 -2.0386 4.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7185 1.7108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 1.2380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0090 1.6794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9860 2.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5037 2.5859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9745 1.5841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9745 -0.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7185 -0.1806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3255 1.6394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5144 3.9872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 2.4049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8994 1.2380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5016 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3992 3.5804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3053 1.9981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5375 0.2922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3533 1.2741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3072 2.8151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9202 1.5841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9202 -0.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5559 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8994 0.2922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3486 2.4099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3931 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3234 3.3994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3565 -0.1806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3832 0.2746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3931 2.4031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3931 -0.8729 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 -1.0742 2.6699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 14 1 0 0 0 0 3 18 1 0 0 0 0 4 5 2 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 17 1 0 0 0 0 7 15 2 0 0 0 0 7 21 1 0 0 0 0 8 15 1 0 0 0 0 8 22 2 0 0 0 0 9 14 1 0 0 0 0 9 23 2 0 0 0 0 10 18 2 0 0 0 0 10 24 1 0 0 0 0 11 19 2 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 27 1 0 0 0 0 13 17 2 0 0 0 0 13 27 1 0 0 0 0 14 24 2 0 0 0 0 15 23 1 0 0 0 0 16 6 1 6 0 0 0 16 20 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 27 1 1 1 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.14
Volume:	447.95
LogP:	6.263
LogD:	3.743
LogS:	-3.546
# Rotatable Bonds:	2
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	4.635
Fsp3:	0.185
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.966
MDCK Permeability:	1.2734206393361092e-05
Pgp-inhibitor:	0.078
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	97.56932830810547%
Volume Distribution (VD):	0.613
Pgp-substrate:	1.8576791286468506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.662
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.725
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	10.97
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.294
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.624
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.956
Carcinogencity:	0.629
Eye Corrosion:	0.003
Eye Irritation:	0.707
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC159508

Natural Product ID:	NPC159508
*Common Name:**	Mulberrofuran H
IUPAC Name:	n.a.
Synonyms:	Mulberrofuran H
Standard InCHIKey:	ZVTKGVROAGDVCH-OQRWROFFSA-N
Standard InCHI:	InChI=1S/C27H22O6/c1-27-12-16(20-5-4-19(29)11-25(20)33-27)6-17(13-27)26-21(30)7-15(8-22(26)31)23-9-14-2-3-18(28)10-24(14)32-23/h2-5,7-11,13,16,28-31H,6,12H2,1H3/t16-,27-/m0/s1
SMILES:	Oc1ccc2c(c1)O[C@]1(C[C@@H]2CC(=C1)c1c(O)cc(cc1O)c1oc2c(c1)ccc(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563553
PubChem CID:	20056162
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
NPO2578	Morus sp.	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072214]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	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]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	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	4

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	140.0	nM	PMID[543159]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	3200.0	nM	PMID[543160]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	15400.0	nM	PMID[543159]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	30000.0	nM	PMID[543159]

☑ 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 NPC159508 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	444
0.1-0.2	1830
0.2-0.3	3965
0.3-0.4	10076
0.4-0.5	8338
0.5-0.6	3859
0.6-0.7	5735
0.7-0.8	5269
0.8-0.85	2543
0.85-0.9	600
0.9-0.95	29
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9682	High Similarity	NPC169471
0.956	High Similarity	NPC253730
0.956	High Similarity	NPC286230
0.9484	High Similarity	NPC137100
0.9444	High Similarity	NPC59491
0.9444	High Similarity	NPC24748
0.9355	High Similarity	NPC72370
0.9333	High Similarity	NPC121888
0.9329	High Similarity	NPC101991
0.9286	High Similarity	NPC167576
0.9231	High Similarity	NPC472462
0.9226	High Similarity	NPC149085
0.9177	High Similarity	NPC65504
0.9177	High Similarity	NPC164110
0.9177	High Similarity	NPC212967
0.9177	High Similarity	NPC268360
0.9177	High Similarity	NPC246647
0.9177	High Similarity	NPC96342
0.9172	High Similarity	NPC99199
0.9161	High Similarity	NPC230713
0.9161	High Similarity	NPC78335
0.9119	High Similarity	NPC472877
0.9119	High Similarity	NPC226287
0.9114	High Similarity	NPC180924
0.9108	High Similarity	NPC213608
0.9108	High Similarity	NPC235333
0.9108	High Similarity	NPC1477
0.9103	High Similarity	NPC170169
0.9103	High Similarity	NPC193976
0.9103	High Similarity	NPC23668
0.9097	High Similarity	NPC178202
0.9051	High Similarity	NPC213936
0.9051	High Similarity	NPC148938
0.9051	High Similarity	NPC297531
0.9045	High Similarity	NPC5871
0.9045	High Similarity	NPC207624
0.9045	High Similarity	NPC142308
0.9036	High Similarity	NPC300657
0.9012	High Similarity	NPC38591
0.9012	High Similarity	NPC473009
0.9006	High Similarity	NPC301256
0.9006	High Similarity	NPC312273
0.9	High Similarity	NPC40583
0.8981	High Similarity	NPC115324
0.8981	High Similarity	NPC58668
0.8981	High Similarity	NPC106372
0.8974	High Similarity	NPC226644
0.8974	High Similarity	NPC37226
0.8974	High Similarity	NPC221868
0.8974	High Similarity	NPC37208
0.8968	High Similarity	NPC17816
0.8968	High Similarity	NPC150215
0.8961	High Similarity	NPC155144
0.8957	High Similarity	NPC473010
0.8957	High Similarity	NPC474591
0.8951	High Similarity	NPC477239
0.8951	High Similarity	NPC473012
0.8951	High Similarity	NPC3448
0.8931	High Similarity	NPC198490
0.891	High Similarity	NPC272194
0.891	High Similarity	NPC135325
0.8903	High Similarity	NPC196114
0.8903	High Similarity	NPC210826
0.8902	High Similarity	NPC251336
0.8896	High Similarity	NPC155640
0.8889	High Similarity	NPC137232
0.8889	High Similarity	NPC30655
0.8889	High Similarity	NPC74854
0.8889	High Similarity	NPC18380
0.8889	High Similarity	NPC45124
0.8882	High Similarity	NPC177650
0.8882	High Similarity	NPC51760
0.8882	High Similarity	NPC244750
0.8882	High Similarity	NPC105584
0.8875	High Similarity	NPC54830
0.8875	High Similarity	NPC56049
0.8868	High Similarity	NPC329844
0.8868	High Similarity	NPC183874
0.8862	High Similarity	NPC473834
0.8862	High Similarity	NPC65885
0.8861	High Similarity	NPC305965
0.8855	High Similarity	NPC476641
0.8848	High Similarity	NPC50394
0.8846	High Similarity	NPC130581
0.8846	High Similarity	NPC12148
0.8839	High Similarity	NPC230943
0.8839	High Similarity	NPC98926
0.8834	High Similarity	NPC15374
0.8834	High Similarity	NPC473011
0.8827	High Similarity	NPC312993
0.8827	High Similarity	NPC186325
0.8827	High Similarity	NPC115432
0.8827	High Similarity	NPC195136
0.8827	High Similarity	NPC260296
0.8827	High Similarity	NPC184326
0.8827	High Similarity	NPC292863
0.882	High Similarity	NPC260902
0.882	High Similarity	NPC296957
0.8812	High Similarity	NPC275575
0.8805	High Similarity	NPC142527
0.8802	High Similarity	NPC477529
0.8797	High Similarity	NPC29777
0.8797	High Similarity	NPC13282
0.8797	High Similarity	NPC120105
0.8797	High Similarity	NPC101957
0.8797	High Similarity	NPC471115
0.8795	High Similarity	NPC53252
0.879	High Similarity	NPC37135
0.879	High Similarity	NPC186397
0.879	High Similarity	NPC39195
0.8788	High Similarity	NPC277480
0.8782	High Similarity	NPC51641
0.8782	High Similarity	NPC299011
0.8782	High Similarity	NPC477955
0.8782	High Similarity	NPC300267
0.8774	High Similarity	NPC225884
0.8774	High Similarity	NPC302181
0.8773	High Similarity	NPC189552
0.8773	High Similarity	NPC273467
0.8765	High Similarity	NPC474373
0.8765	High Similarity	NPC195167
0.8758	High Similarity	NPC309648
0.8758	High Similarity	NPC247677
0.8758	High Similarity	NPC69531
0.8758	High Similarity	NPC61112
0.8758	High Similarity	NPC160015
0.8758	High Similarity	NPC198489
0.8758	High Similarity	NPC32867
0.8757	High Similarity	NPC8127
0.8757	High Similarity	NPC49667
0.875	High Similarity	NPC310794
0.875	High Similarity	NPC290830
0.875	High Similarity	NPC147363
0.875	High Similarity	NPC82217
0.875	High Similarity	NPC178964
0.875	High Similarity	NPC303485
0.875	High Similarity	NPC194593
0.875	High Similarity	NPC476640
0.875	High Similarity	NPC73899
0.875	High Similarity	NPC72425
0.875	High Similarity	NPC71061
0.875	High Similarity	NPC280530
0.875	High Similarity	NPC17105
0.875	High Similarity	NPC474276
0.875	High Similarity	NPC122365
0.875	High Similarity	NPC95842
0.875	High Similarity	NPC216842
0.8743	High Similarity	NPC131866
0.8742	High Similarity	NPC474417
0.8742	High Similarity	NPC138299
0.8742	High Similarity	NPC258249
0.8742	High Similarity	NPC222713
0.8742	High Similarity	NPC67322
0.8742	High Similarity	NPC149526
0.8742	High Similarity	NPC111112
0.8735	High Similarity	NPC470704
0.8735	High Similarity	NPC476459
0.8734	High Similarity	NPC223988
0.8734	High Similarity	NPC296030
0.8734	High Similarity	NPC266499
0.8734	High Similarity	NPC39929
0.8734	High Similarity	NPC474052
0.8734	High Similarity	NPC65775
0.8734	High Similarity	NPC329933
0.8734	High Similarity	NPC10027
0.8727	High Similarity	NPC37183
0.8727	High Similarity	NPC136641
0.8726	High Similarity	NPC308200
0.872	High Similarity	NPC475106
0.8718	High Similarity	NPC184649
0.8718	High Similarity	NPC311144
0.8718	High Similarity	NPC303185
0.8712	High Similarity	NPC121647
0.8712	High Similarity	NPC472060
0.8712	High Similarity	NPC470810
0.8712	High Similarity	NPC472618
0.8712	High Similarity	NPC470342
0.8712	High Similarity	NPC472052
0.8712	High Similarity	NPC304839
0.8712	High Similarity	NPC220582
0.871	High Similarity	NPC144499
0.871	High Similarity	NPC1534
0.871	High Similarity	NPC53192
0.8704	High Similarity	NPC287789
0.8704	High Similarity	NPC475184
0.8704	High Similarity	NPC201127
0.8704	High Similarity	NPC196448
0.8704	High Similarity	NPC271741
0.8698	High Similarity	NPC287243
0.8696	High Similarity	NPC201227
0.8696	High Similarity	NPC226656
0.8696	High Similarity	NPC159707
0.8696	High Similarity	NPC182555
0.8696	High Similarity	NPC186227
0.8696	High Similarity	NPC265624
0.8696	High Similarity	NPC52611
0.8696	High Similarity	NPC121649
0.8696	High Similarity	NPC134171
0.8696	High Similarity	NPC248739
0.8696	High Similarity	NPC14606

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 NPC159508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	985
0.2-0.3	1527
0.3-0.4	2679
0.4-0.5	1976
0.5-0.6	1052
0.6-0.7	347
0.7-0.8	132
0.8-0.85	44
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD3749	Approved
0.8773	High Similarity	NPD6959	Discontinued
0.8599	High Similarity	NPD7410	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD6559	Discontinued
0.8293	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7411	Suspended
0.8269	Intermediate Similarity	NPD2344	Approved
0.8263	Intermediate Similarity	NPD5494	Approved
0.8235	Intermediate Similarity	NPD7473	Discontinued
0.8217	Intermediate Similarity	NPD1549	Phase 2
0.8193	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD7390	Discontinued
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.8166	Intermediate Similarity	NPD6232	Discontinued
0.8165	Intermediate Similarity	NPD2800	Approved
0.8153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1607	Approved
0.8121	Intermediate Similarity	NPD1934	Approved
0.811	Intermediate Similarity	NPD4380	Phase 2
0.8084	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD1511	Approved
0.8072	Intermediate Similarity	NPD2801	Approved
0.8063	Intermediate Similarity	NPD2309	Approved
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7976	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1512	Approved
0.7975	Intermediate Similarity	NPD2796	Approved
0.7975	Intermediate Similarity	NPD6100	Approved
0.7975	Intermediate Similarity	NPD6099	Approved
0.7939	Intermediate Similarity	NPD3226	Approved
0.7937	Intermediate Similarity	NPD1243	Approved
0.7929	Intermediate Similarity	NPD7075	Discontinued
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3926	Phase 2
0.7889	Intermediate Similarity	NPD4287	Approved
0.7874	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7054	Approved
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7688	Intermediate Similarity	NPD1247	Approved
0.7688	Intermediate Similarity	NPD3748	Approved
0.7688	Intermediate Similarity	NPD2799	Discontinued
0.7684	Intermediate Similarity	NPD7472	Approved
0.7683	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1465	Phase 2
0.7643	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5408	Approved
0.764	Intermediate Similarity	NPD6797	Phase 2
0.764	Intermediate Similarity	NPD5406	Approved
0.764	Intermediate Similarity	NPD5404	Approved
0.764	Intermediate Similarity	NPD5405	Approved
0.764	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7636	Intermediate Similarity	NPD6799	Approved
0.7628	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3817	Phase 2
0.7598	Intermediate Similarity	NPD7251	Discontinued
0.7596	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6801	Discontinued
0.758	Intermediate Similarity	NPD4625	Phase 3
0.7572	Intermediate Similarity	NPD919	Approved
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7556	Intermediate Similarity	NPD7808	Phase 3
0.7556	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5761	Phase 2
0.7544	Intermediate Similarity	NPD5760	Phase 2
0.7543	Intermediate Similarity	NPD5710	Approved
0.7543	Intermediate Similarity	NPD5711	Approved
0.7543	Intermediate Similarity	NPD7229	Phase 3
0.7532	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD2296	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1471	Phase 3
0.7459	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7003	Approved
0.7453	Intermediate Similarity	NPD6651	Approved
0.7438	Intermediate Similarity	NPD943	Approved
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD3764	Approved
0.7396	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8150	Discontinued
0.7374	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4628	Phase 3
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7345	Intermediate Similarity	NPD3787	Discontinued
0.7337	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.733	Intermediate Similarity	NPD6779	Approved
0.733	Intermediate Similarity	NPD6776	Approved
0.733	Intermediate Similarity	NPD6780	Approved
0.733	Intermediate Similarity	NPD6781	Approved
0.733	Intermediate Similarity	NPD6777	Approved
0.733	Intermediate Similarity	NPD6778	Approved
0.733	Intermediate Similarity	NPD6782	Approved
0.7325	Intermediate Similarity	NPD1470	Approved
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.7294	Intermediate Similarity	NPD5403	Approved
0.7278	Intermediate Similarity	NPD7177	Discontinued
0.7278	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7256	Intermediate Similarity	NPD4308	Phase 3
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7216	Intermediate Similarity	NPD7697	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7205	Intermediate Similarity	NPD3268	Approved
0.7191	Intermediate Similarity	NPD7199	Phase 2
0.7184	Intermediate Similarity	NPD6280	Approved
0.7184	Intermediate Similarity	NPD6279	Approved
0.7184	Intermediate Similarity	NPD37	Approved
0.7182	Intermediate Similarity	NPD7228	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7179	Intermediate Similarity	NPD1201	Approved
0.7176	Intermediate Similarity	NPD5401	Approved
0.7175	Intermediate Similarity	NPD6234	Discontinued
0.7167	Intermediate Similarity	NPD2403	Approved
0.7159	Intermediate Similarity	NPD4965	Approved
0.7159	Intermediate Similarity	NPD4966	Approved
0.7159	Intermediate Similarity	NPD4967	Phase 2
0.7135	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2797	Approved
0.7102	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4288	Approved
0.7099	Intermediate Similarity	NPD411	Approved
0.7081	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6823	Phase 2
0.7073	Intermediate Similarity	NPD447	Suspended
0.7071	Intermediate Similarity	NPD7701	Phase 2
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6535	Approved
0.7068	Intermediate Similarity	NPD6534	Approved
0.7062	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6808	Phase 2
0.705	Intermediate Similarity	NPD7801	Approved
0.7048	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.7033	Intermediate Similarity	NPD3446	Phase 1
0.7029	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3972	Approved
0.7025	Intermediate Similarity	NPD9717	Approved
0.7019	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2861	Phase 2
0.7012	Intermediate Similarity	NPD4307	Phase 2
0.7011	Intermediate Similarity	NPD1729	Discontinued
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6844	Discontinued
0.6989	Remote Similarity	NPD7577	Discontinued
0.6983	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2654	Approved
0.6975	Remote Similarity	NPD6832	Phase 2
0.697	Remote Similarity	NPD5123	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