NPASS Compound

Structure

CID53640 OpenBabel06191715392D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.6691 -4.4530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1691 -3.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1691 -1.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2141 2.8554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2141 1.8554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1691 -1.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6691 -2.7210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6691 -0.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1691 -0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1691 -0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8535 1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1691 -3.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6691 -0.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8480 1.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3480 2.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1691 1.6092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8480 3.2215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2548 0.5759 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 18 2 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 25 2 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 26 2 0 0 0 0 16 23 1 0 0 0 0 16 27 1 0 0 0 0 19 28 2 0 0 0 0 20 30 1 0 0 0 0 21 24 2 0 0 0 0 21 28 1 0 0 0 0 22 23 2 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 31 1 0 0 0 0 25 34 1 0 0 0 0 26 33 1 0 0 0 0 27 29 1 6 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.24
Volume:	496.137
LogP:	7.042
LogD:	4.586
LogS:	-2.869
# Rotatable Bonds:	7
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	3.784
Fsp3:	0.379
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:	-4.836
MDCK Permeability:	1.504674492025515e-05
Pgp-inhibitor:	0.89
Pgp-substrate:	0.175
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.417

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.49634552001953%
Volume Distribution (VD):	0.886
Pgp-substrate:	1.8713418245315552%

ADMET: Metabolism

CYP1A2-inhibitor:	0.718
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.844
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	7.601
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.963
Drug-inuced Liver Injury (DILI):	0.523
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.654
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.087
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC53640

Natural Product ID:	NPC53640
*Common Name:**	Mulberrofuran X
IUPAC Name:	7-[(2E)-3,7-dimethylocta-2,6-dienyl]-2-[(2R)-6-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-4-yl]-1-benzofuran-6-ol
Synonyms:	Mulberrofuran X
Standard InCHIKey:	HDAQXXCKXVBBEI-XHLFLETQSA-N
Standard InCHI:	InChI=1S/C29H34O5/c1-17(2)7-6-8-18(3)9-11-21-24(31)12-10-19-13-25(34-28(19)21)22-14-20(30)15-26-23(22)16-27(33-26)29(4,5)32/h7,9-10,12-15,27,30-32H,6,8,11,16H2,1-5H3/b18-9+/t27-/m1/s1
SMILES:	CC(=CCC/C(=C/Cc1c(ccc2cc(c3cc(cc4c3C[C@H](C(C)(C)O)O4)O)oc12)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459623
PubChem CID:	11798274
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	290000.0	nM	PMID[476186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	260000.0	nM	PMID[476186]
NPT27	Others	Unspecified		CC50	=	350000.0	nM	PMID[476186]
NPT27	Others	Unspecified		Ratio	=	1.2	n.a.	PMID[476186]

☑ 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 NPC53640 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	411
0.1-0.2	1538
0.2-0.3	3358
0.3-0.4	8777
0.4-0.5	9798
0.5-0.6	3709
0.6-0.7	5079
0.7-0.8	5340
0.8-0.85	2898
0.85-0.9	1673
0.9-0.95	113
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9679	High Similarity	NPC220582
0.9679	High Similarity	NPC304839
0.9423	High Similarity	NPC297531
0.9423	High Similarity	NPC148938
0.9423	High Similarity	NPC213936
0.9371	High Similarity	NPC74854
0.9371	High Similarity	NPC45124
0.9371	High Similarity	NPC30655
0.9359	High Similarity	NPC235333
0.9321	High Similarity	NPC476459
0.9304	High Similarity	NPC246647
0.9304	High Similarity	NPC96342
0.9304	High Similarity	NPC268360
0.9304	High Similarity	NPC164110
0.9304	High Similarity	NPC212967
0.9295	High Similarity	NPC207624
0.9295	High Similarity	NPC142308
0.9245	High Similarity	NPC40583
0.9241	High Similarity	NPC180924
0.9231	High Similarity	NPC23668
0.9231	High Similarity	NPC193976
0.9231	High Similarity	NPC58668
0.9231	High Similarity	NPC106372
0.9231	High Similarity	NPC170169
0.9231	High Similarity	NPC115324
0.9207	High Similarity	NPC120220
0.9187	High Similarity	NPC470810
0.9177	High Similarity	NPC99199
0.9177	High Similarity	NPC198490
0.9167	High Similarity	NPC472421
0.9167	High Similarity	NPC230713
0.9167	High Similarity	NPC78335
0.9152	High Similarity	NPC472584
0.9136	High Similarity	NPC472581
0.9114	High Similarity	NPC213608
0.9114	High Similarity	NPC183874
0.9114	High Similarity	NPC1477
0.9114	High Similarity	NPC472462
0.9108	High Similarity	NPC474744
0.9108	High Similarity	NPC474772
0.9108	High Similarity	NPC472423
0.9103	High Similarity	NPC178202
0.9103	High Similarity	NPC226644
0.9103	High Similarity	NPC37226
0.9085	High Similarity	NPC247973
0.908	High Similarity	NPC39306
0.908	High Similarity	NPC300053
0.9074	High Similarity	NPC219861
0.9074	High Similarity	NPC472402
0.9062	High Similarity	NPC296957
0.9062	High Similarity	NPC65504
0.9062	High Similarity	NPC260902
0.9051	High Similarity	NPC5871
0.9051	High Similarity	NPC477957
0.9051	High Similarity	NPC473996
0.9051	High Similarity	NPC476238
0.9051	High Similarity	NPC327269
0.9051	High Similarity	NPC31627
0.9038	High Similarity	NPC135325
0.9024	High Similarity	NPC119589
0.9024	High Similarity	NPC277480
0.9018	High Similarity	NPC472582
0.9018	High Similarity	NPC133065
0.9012	High Similarity	NPC96031
0.9006	High Similarity	NPC476349
0.9006	High Similarity	NPC476350
0.9	High Similarity	NPC247677
0.9	High Similarity	NPC160015
0.8988	High Similarity	NPC312630
0.8988	High Similarity	NPC324220
0.8987	High Similarity	NPC472636
0.8987	High Similarity	NPC472580
0.8987	High Similarity	NPC471675
0.8982	High Similarity	NPC310794
0.8981	High Similarity	NPC296030
0.8981	High Similarity	NPC39929
0.8976	High Similarity	NPC131866
0.8974	High Similarity	NPC14875
0.8974	High Similarity	NPC130581
0.8974	High Similarity	NPC17816
0.8974	High Similarity	NPC12148
0.8963	High Similarity	NPC37183
0.8957	High Similarity	NPC84515
0.8957	High Similarity	NPC312056
0.8951	High Similarity	NPC328102
0.8931	High Similarity	NPC285623
0.8929	High Similarity	NPC227906
0.8924	High Similarity	NPC13282
0.8924	High Similarity	NPC167576
0.891	High Similarity	NPC210826
0.891	High Similarity	NPC51641
0.891	High Similarity	NPC300267
0.8909	High Similarity	NPC170245
0.8902	High Similarity	NPC124038
0.8902	High Similarity	NPC109180
0.8902	High Similarity	NPC471286
0.8896	High Similarity	NPC304387
0.8896	High Similarity	NPC3629
0.8896	High Similarity	NPC188486
0.8896	High Similarity	NPC92589
0.8896	High Similarity	NPC269117
0.8889	High Similarity	NPC210459
0.8882	High Similarity	NPC208152
0.8882	High Similarity	NPC78492
0.8882	High Similarity	NPC104682
0.8875	High Similarity	NPC100134
0.8875	High Similarity	NPC72370
0.8875	High Similarity	NPC210942
0.8875	High Similarity	NPC303950
0.8875	High Similarity	NPC209760
0.8875	High Similarity	NPC169990
0.8875	High Similarity	NPC122365
0.8868	High Similarity	NPC244577
0.8868	High Similarity	NPC471677
0.8868	High Similarity	NPC471676
0.8868	High Similarity	NPC472420
0.8868	High Similarity	NPC263384
0.8868	High Similarity	NPC472422
0.8861	High Similarity	NPC317492
0.8861	High Similarity	NPC65775
0.8861	High Similarity	NPC221868
0.8861	High Similarity	NPC37208
0.8861	High Similarity	NPC10027
0.8855	High Similarity	NPC50394
0.8855	High Similarity	NPC150131
0.8848	High Similarity	NPC108433
0.8848	High Similarity	NPC326520
0.8848	High Similarity	NPC472277
0.8848	High Similarity	NPC474591
0.8848	High Similarity	NPC136641
0.8848	High Similarity	NPC293319
0.8846	High Similarity	NPC155144
0.8846	High Similarity	NPC98926
0.8846	High Similarity	NPC230943
0.8841	High Similarity	NPC272722
0.8841	High Similarity	NPC472964
0.8841	High Similarity	NPC201800
0.8834	High Similarity	NPC472624
0.8834	High Similarity	NPC321399
0.8834	High Similarity	NPC36217
0.8834	High Similarity	NPC471976
0.8834	High Similarity	NPC299436
0.8827	High Similarity	NPC196448
0.882	High Similarity	NPC477958
0.8812	High Similarity	NPC210597
0.8812	High Similarity	NPC263676
0.8812	High Similarity	NPC67654
0.8812	High Similarity	NPC253872
0.8805	High Similarity	NPC476509
0.8802	High Similarity	NPC211309
0.8802	High Similarity	NPC53252
0.8802	High Similarity	NPC288813
0.8797	High Similarity	NPC272194
0.8797	High Similarity	NPC168085
0.8795	High Similarity	NPC235610
0.879	High Similarity	NPC316769
0.8788	High Similarity	NPC205265
0.8788	High Similarity	NPC18100
0.8788	High Similarity	NPC475985
0.8788	High Similarity	NPC186686
0.8788	High Similarity	NPC91288
0.8788	High Similarity	NPC472281
0.8782	High Similarity	NPC302181
0.8782	High Similarity	NPC225884
0.878	High Similarity	NPC474187
0.878	High Similarity	NPC474186
0.878	High Similarity	NPC14822
0.8779	High Similarity	NPC475148
0.8779	High Similarity	NPC475656
0.8773	High Similarity	NPC16935
0.8773	High Similarity	NPC196879
0.8765	High Similarity	NPC478223
0.8765	High Similarity	NPC24640
0.8765	High Similarity	NPC45131
0.8758	High Similarity	NPC7989
0.8758	High Similarity	NPC293286
0.8758	High Similarity	NPC472583
0.8758	High Similarity	NPC223701
0.8758	High Similarity	NPC469405
0.8757	High Similarity	NPC98776
0.8757	High Similarity	NPC277510
0.875	High Similarity	NPC116604
0.875	High Similarity	NPC471229
0.875	High Similarity	NPC232645
0.875	High Similarity	NPC478148
0.875	High Similarity	NPC156244
0.875	High Similarity	NPC149526
0.875	High Similarity	NPC72958
0.875	High Similarity	NPC313717
0.875	High Similarity	NPC474417
0.875	High Similarity	NPC315306
0.8743	High Similarity	NPC320789
0.8743	High Similarity	NPC218226
0.8742	High Similarity	NPC472628
0.8736	High Similarity	NPC73929
0.8736	High Similarity	NPC139683
0.8736	High Similarity	NPC47905
0.8735	High Similarity	NPC38914
0.8735	High Similarity	NPC204088
0.8735	High Similarity	NPC291110

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 NPC53640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	900
0.2-0.3	1624
0.3-0.4	2602
0.4-0.5	1935
0.5-0.6	1074
0.6-0.7	452
0.7-0.8	152
0.8-0.85	45
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD2393	Clinical (unspecified phase)
0.8538	High Similarity	NPD6559	Discontinued
0.8537	High Similarity	NPD3882	Suspended
0.8528	High Similarity	NPD7819	Suspended
0.8485	Intermediate Similarity	NPD3749	Approved
0.8485	Intermediate Similarity	NPD7075	Discontinued
0.8466	Intermediate Similarity	NPD1934	Approved
0.8457	Intermediate Similarity	NPD4380	Phase 2
0.8443	Intermediate Similarity	NPD6959	Discontinued
0.8415	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7473	Discontinued
0.8304	Intermediate Similarity	NPD3818	Discontinued
0.8303	Intermediate Similarity	NPD2801	Approved
0.8284	Intermediate Similarity	NPD6232	Discontinued
0.8261	Intermediate Similarity	NPD2534	Approved
0.8261	Intermediate Similarity	NPD2533	Approved
0.8261	Intermediate Similarity	NPD2532	Approved
0.8261	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD2344	Approved
0.816	Intermediate Similarity	NPD920	Approved
0.8155	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD5844	Phase 1
0.8133	Intermediate Similarity	NPD6801	Discontinued
0.8129	Intermediate Similarity	NPD3926	Phase 2
0.8118	Intermediate Similarity	NPD1247	Approved
0.8101	Intermediate Similarity	NPD2796	Approved
0.8095	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7768	Phase 2
0.8086	Intermediate Similarity	NPD1511	Approved
0.8086	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8063	Intermediate Similarity	NPD2800	Approved
0.8046	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8037	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD1512	Approved
0.7977	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2309	Approved
0.795	Intermediate Similarity	NPD1243	Approved
0.7943	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1607	Approved
0.7898	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD5402	Approved
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD3750	Approved
0.779	Intermediate Similarity	NPD8434	Phase 2
0.7765	Intermediate Similarity	NPD1465	Phase 2
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD2935	Discontinued
0.7759	Intermediate Similarity	NPD7229	Phase 3
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.7738	Intermediate Similarity	NPD3226	Approved
0.773	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD8312	Approved
0.7705	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5761	Phase 2
0.7661	Intermediate Similarity	NPD5760	Phase 2
0.7657	Intermediate Similarity	NPD5710	Approved
0.7657	Intermediate Similarity	NPD5711	Approved
0.7654	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7390	Discontinued
0.764	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD5403	Approved
0.7607	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2346	Discontinued
0.76	Intermediate Similarity	NPD7199	Phase 2
0.7593	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7572	Intermediate Similarity	NPD4965	Approved
0.7569	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD943	Approved
0.7557	Intermediate Similarity	NPD3787	Discontinued
0.7556	Intermediate Similarity	NPD5953	Discontinued
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6099	Approved
0.7546	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD5401	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7486	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD3748	Approved
0.7469	Intermediate Similarity	NPD6651	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7427	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2296	Approved
0.7412	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7783	Phase 2
0.7411	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7405	Intermediate Similarity	NPD8150	Discontinued
0.7399	Intermediate Similarity	NPD37	Approved
0.7378	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4625	Phase 3
0.7371	Intermediate Similarity	NPD7871	Phase 2
0.7371	Intermediate Similarity	NPD7870	Phase 2
0.7368	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3764	Approved
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7698	Approved
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD6280	Approved
0.7299	Intermediate Similarity	NPD6279	Approved
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7263	Intermediate Similarity	NPD6808	Phase 2
0.7259	Intermediate Similarity	NPD7701	Phase 2
0.7246	Intermediate Similarity	NPD2424	Discontinued
0.7239	Intermediate Similarity	NPD4060	Phase 1
0.7239	Intermediate Similarity	NPD1613	Approved
0.7239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5405	Approved
0.7229	Intermediate Similarity	NPD5404	Approved
0.7229	Intermediate Similarity	NPD5406	Approved
0.7229	Intermediate Similarity	NPD5408	Approved
0.7228	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1729	Discontinued
0.7208	Intermediate Similarity	NPD7584	Approved
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.7195	Intermediate Similarity	NPD447	Suspended
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7193	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7874	Approved
0.7182	Intermediate Similarity	NPD2403	Approved
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.7173	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD6535	Approved
0.7169	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD3027	Phase 3
0.7159	Intermediate Similarity	NPD8455	Phase 2
0.715	Intermediate Similarity	NPD7700	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD7699	Phase 2
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7930	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7125	Intermediate Similarity	NPD1470	Approved
0.7125	Intermediate Similarity	NPD1203	Approved
0.7104	Intermediate Similarity	NPD7177	Discontinued
0.7099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7003	Approved
0.7052	Intermediate Similarity	NPD6273	Approved
0.7043	Intermediate Similarity	NPD7685	Pre-registration
0.7037	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8320	Phase 1
0.702	Intermediate Similarity	NPD8319	Approved
0.7018	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6798	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