NPASS Compound

Structure

CID310794 OpenBabel06191716122D 26 30 0 0 0 0 0 0 0 0999 V2000 1.0167 0.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5087 1.8489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5934 2.4949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8742 1.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0353 0.9699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6778 0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7135 0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6784 -1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0358 -1.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7133 0.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0354 0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6780 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 -1.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 -1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8393 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8745 -0.4832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1961 -0.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5176 -0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8391 -0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0266 -1.9537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5935 1.4785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8747 -1.4526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3570 0.0008 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.12
Volume:	351.849
LogP:	5.118
LogD:	4.467
LogS:	-5.163
# Rotatable Bonds:	1
TPSA:	61.06
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	3.086
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.884
MDCK Permeability:	1.6658368622302078e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	98.1529312133789%
Volume Distribution (VD):	0.515
Pgp-substrate:	4.323442459106445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.793
CYP2C19-inhibitor:	0.811
CYP2C19-substrate:	0.174
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.617
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.598
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	8.318
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.673
Skin Sensitization:	0.49
Carcinogencity:	0.8
Eye Corrosion:	0.003
Eye Irritation:	0.074
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC310794

Natural Product ID:	NPC310794
*Common Name:**	Lespeflorin H2
IUPAC Name:	n.a.
Synonyms:	Lespeflorin H2
Standard InCHIKey:	AMXXXMGWYLGBLR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H18O5/c1-21(2)7-6-13-19-14(9-16(22)20(13)26-21)15-10-24-17-8-11(23-3)4-5-12(17)18(15)25-19/h4-9,22H,10H2,1-3H3
SMILES:	CC1(C)C=Cc2c3c(cc(c2O1)O)c1COc2cc(ccc2-c1o3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550432
PubChem CID:	25227612
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1480.0	nM	PMID[481261]

☑ 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 NPC310794 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	436
0.1-0.2	1903
0.2-0.3	4379
0.3-0.4	11042
0.4-0.5	6926
0.5-0.6	3691
0.6-0.7	5181
0.7-0.8	5186
0.8-0.85	2319
0.85-0.9	1238
0.9-0.95	392
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC277480
0.963	High Similarity	NPC247973
0.9627	High Similarity	NPC37183
0.9512	High Similarity	NPC131866
0.9512	High Similarity	NPC472276
0.9503	High Similarity	NPC84515
0.9503	High Similarity	NPC312056
0.9503	High Similarity	NPC472448
0.9503	High Similarity	NPC83922
0.9455	High Similarity	NPC174700
0.9451	High Similarity	NPC288813
0.9441	High Similarity	NPC188486
0.9441	High Similarity	NPC29876
0.9441	High Similarity	NPC167678
0.9401	High Similarity	NPC164384
0.9398	High Similarity	NPC473834
0.939	High Similarity	NPC50394
0.9387	High Similarity	NPC275780
0.9387	High Similarity	NPC472450
0.9387	High Similarity	NPC239752
0.9383	High Similarity	NPC474162
0.9383	High Similarity	NPC261470
0.9383	High Similarity	NPC474150
0.9383	High Similarity	NPC81679
0.9379	High Similarity	NPC476980
0.9379	High Similarity	NPC204290
0.9341	High Similarity	NPC227906
0.9337	High Similarity	NPC248593
0.9337	High Similarity	NPC28589
0.9333	High Similarity	NPC152477
0.9329	High Similarity	NPC39091
0.9329	High Similarity	NPC235610
0.9329	High Similarity	NPC173292
0.9329	High Similarity	NPC170245
0.9325	High Similarity	NPC133065
0.9325	High Similarity	NPC189473
0.9325	High Similarity	NPC23298
0.9325	High Similarity	NPC124038
0.9325	High Similarity	NPC303460
0.9325	High Similarity	NPC306321
0.9321	High Similarity	NPC259456
0.9317	High Similarity	NPC16935
0.9317	High Similarity	NPC196879
0.9317	High Similarity	NPC204879
0.9286	High Similarity	NPC8127
0.9286	High Similarity	NPC49667
0.9281	High Similarity	NPC261471
0.9268	High Similarity	NPC108433
0.9268	High Similarity	NPC326520
0.9268	High Similarity	NPC472277
0.9268	High Similarity	NPC50960
0.9268	High Similarity	NPC300053
0.9268	High Similarity	NPC36320
0.9268	High Similarity	NPC39306
0.9268	High Similarity	NPC45449
0.9264	High Similarity	NPC329760
0.9264	High Similarity	NPC229632
0.9259	High Similarity	NPC192686
0.9259	High Similarity	NPC118256
0.9259	High Similarity	NPC472624
0.9259	High Similarity	NPC119209
0.9259	High Similarity	NPC328102
0.9255	High Similarity	NPC262286
0.9255	High Similarity	NPC36852
0.9255	High Similarity	NPC65504
0.9255	High Similarity	NPC476981
0.9255	High Similarity	NPC52889
0.9255	High Similarity	NPC218313
0.9255	High Similarity	NPC474681
0.9255	High Similarity	NPC78225
0.9235	High Similarity	NPC97523
0.9226	High Similarity	NPC287243
0.9222	High Similarity	NPC475825
0.9222	High Similarity	NPC223375
0.9222	High Similarity	NPC121333
0.9217	High Similarity	NPC242395
0.9212	High Similarity	NPC120593
0.9212	High Similarity	NPC128293
0.9212	High Similarity	NPC37870
0.9212	High Similarity	NPC472449
0.9207	High Similarity	NPC18100
0.9207	High Similarity	NPC329669
0.9207	High Similarity	NPC472281
0.9207	High Similarity	NPC39305
0.9207	High Similarity	NPC1706
0.9207	High Similarity	NPC186686
0.9207	High Similarity	NPC248638
0.9207	High Similarity	NPC236521
0.9207	High Similarity	NPC152659
0.9207	High Similarity	NPC475985
0.9207	High Similarity	NPC205265
0.9207	High Similarity	NPC473313
0.9207	High Similarity	NPC59295
0.9207	High Similarity	NPC472278
0.9207	High Similarity	NPC41301
0.9207	High Similarity	NPC263092
0.9207	High Similarity	NPC273959
0.9207	High Similarity	NPC1755
0.9202	High Similarity	NPC258331
0.9202	High Similarity	NPC57715
0.9202	High Similarity	NPC30655
0.9202	High Similarity	NPC74854
0.9202	High Similarity	NPC474038
0.9202	High Similarity	NPC134783
0.9202	High Similarity	NPC234644
0.9202	High Similarity	NPC266314
0.9202	High Similarity	NPC61010
0.9202	High Similarity	NPC45124
0.9198	High Similarity	NPC184755
0.9198	High Similarity	NPC74178
0.9198	High Similarity	NPC250214
0.9198	High Similarity	NPC95936
0.9193	High Similarity	NPC45131
0.9193	High Similarity	NPC191146
0.9193	High Similarity	NPC5322
0.9193	High Similarity	NPC138243
0.9193	High Similarity	NPC472455
0.9193	High Similarity	NPC472916
0.9193	High Similarity	NPC133970
0.9193	High Similarity	NPC68093
0.9193	High Similarity	NPC6633
0.9176	High Similarity	NPC183843
0.9167	High Similarity	NPC216842
0.9167	High Similarity	NPC476640
0.9167	High Similarity	NPC37606
0.9167	High Similarity	NPC82217
0.9167	High Similarity	NPC65885
0.9162	High Similarity	NPC78830
0.9162	High Similarity	NPC218533
0.9157	High Similarity	NPC117854
0.9157	High Similarity	NPC8965
0.9157	High Similarity	NPC243877
0.9157	High Similarity	NPC477154
0.9157	High Similarity	NPC6588
0.9152	High Similarity	NPC38914
0.9152	High Similarity	NPC234052
0.9152	High Similarity	NPC224280
0.9152	High Similarity	NPC62261
0.9152	High Similarity	NPC291110
0.9146	High Similarity	NPC476247
0.9146	High Similarity	NPC238995
0.9146	High Similarity	NPC25152
0.9146	High Similarity	NPC474034
0.9146	High Similarity	NPC472635
0.9146	High Similarity	NPC272722
0.9146	High Similarity	NPC472402
0.9146	High Similarity	NPC474033
0.9141	High Similarity	NPC188433
0.9141	High Similarity	NPC471973
0.9141	High Similarity	NPC56085
0.9141	High Similarity	NPC228785
0.9141	High Similarity	NPC475784
0.9141	High Similarity	NPC139036
0.9141	High Similarity	NPC474960
0.9141	High Similarity	NPC14353
0.9136	High Similarity	NPC472914
0.9136	High Similarity	NPC223787
0.9136	High Similarity	NPC129684
0.9136	High Similarity	NPC99597
0.9136	High Similarity	NPC156057
0.9136	High Similarity	NPC27337
0.9136	High Similarity	NPC48208
0.9136	High Similarity	NPC210084
0.9136	High Similarity	NPC245758
0.9136	High Similarity	NPC472911
0.9136	High Similarity	NPC162869
0.9136	High Similarity	NPC284820
0.9136	High Similarity	NPC475267
0.9136	High Similarity	NPC469584
0.9136	High Similarity	NPC472910
0.9136	High Similarity	NPC291508
0.9136	High Similarity	NPC299520
0.9136	High Similarity	NPC181960
0.9136	High Similarity	NPC473272
0.9136	High Similarity	NPC474208
0.9136	High Similarity	NPC222814
0.9136	High Similarity	NPC96167
0.9136	High Similarity	NPC474836
0.9136	High Similarity	NPC472913
0.913	High Similarity	NPC200246
0.913	High Similarity	NPC57674
0.913	High Similarity	NPC2928
0.913	High Similarity	NPC234255
0.913	High Similarity	NPC230149
0.913	High Similarity	NPC117992
0.913	High Similarity	NPC256612
0.913	High Similarity	NPC134287
0.913	High Similarity	NPC130589
0.913	High Similarity	NPC213622
0.913	High Similarity	NPC472280
0.913	High Similarity	NPC168247
0.913	High Similarity	NPC39184
0.913	High Similarity	NPC113906
0.913	High Similarity	NPC256925
0.913	High Similarity	NPC20830
0.913	High Similarity	NPC152951
0.9107	High Similarity	NPC54098
0.9107	High Similarity	NPC230619
0.9102	High Similarity	NPC177480
0.9102	High Similarity	NPC165456

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 NPC310794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	980
0.2-0.3	1780
0.3-0.4	2702
0.4-0.5	1810
0.5-0.6	974
0.6-0.7	338
0.7-0.8	125
0.8-0.85	31
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9068	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD5494	Approved
0.8951	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD1934	Approved
0.8841	High Similarity	NPD3882	Suspended
0.8706	High Similarity	NPD3818	Discontinued
0.8698	High Similarity	NPD6166	Phase 2
0.8698	High Similarity	NPD6168	Clinical (unspecified phase)
0.8698	High Similarity	NPD6167	Clinical (unspecified phase)
0.8631	High Similarity	NPD1247	Approved
0.8547	High Similarity	NPD5844	Phase 1
0.8537	High Similarity	NPD4380	Phase 2
0.8509	High Similarity	NPD1511	Approved
0.8503	High Similarity	NPD4868	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7054	Approved
0.8405	Intermediate Similarity	NPD1512	Approved
0.84	Intermediate Similarity	NPD6559	Discontinued
0.8391	Intermediate Similarity	NPD7472	Approved
0.8391	Intermediate Similarity	NPD7074	Phase 3
0.8363	Intermediate Similarity	NPD6232	Discontinued
0.8344	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8324	Intermediate Similarity	NPD7473	Discontinued
0.8314	Intermediate Similarity	NPD3926	Phase 2
0.8294	Intermediate Similarity	NPD919	Approved
0.8239	Intermediate Similarity	NPD6797	Phase 2
0.8235	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7075	Discontinued
0.8225	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD6959	Discontinued
0.8192	Intermediate Similarity	NPD7251	Discontinued
0.8166	Intermediate Similarity	NPD1465	Phase 2
0.8166	Intermediate Similarity	NPD7819	Suspended
0.8166	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7411	Suspended
0.8146	Intermediate Similarity	NPD7808	Phase 3
0.8086	Intermediate Similarity	NPD1549	Phase 2
0.8057	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD920	Approved
0.8023	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1510	Phase 2
0.8012	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7768	Phase 2
0.7963	Intermediate Similarity	NPD2796	Approved
0.7914	Intermediate Similarity	NPD2344	Approved
0.7904	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6799	Approved
0.7818	Intermediate Similarity	NPD2800	Approved
0.7818	Intermediate Similarity	NPD1243	Approved
0.7814	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2533	Approved
0.7798	Intermediate Similarity	NPD2534	Approved
0.7798	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7764	Intermediate Similarity	NPD1240	Approved
0.7764	Intermediate Similarity	NPD943	Approved
0.7744	Intermediate Similarity	NPD2935	Discontinued
0.7725	Intermediate Similarity	NPD2309	Approved
0.7706	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1607	Approved
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7665	Intermediate Similarity	NPD3750	Approved
0.7605	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5403	Approved
0.7584	Intermediate Similarity	NPD7199	Phase 2
0.7581	Intermediate Similarity	NPD8434	Phase 2
0.7571	Intermediate Similarity	NPD6234	Discontinued
0.7554	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1613	Approved
0.7546	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD5401	Approved
0.7473	Intermediate Similarity	NPD7228	Approved
0.7457	Intermediate Similarity	NPD1653	Approved
0.7453	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7390	Discontinued
0.7427	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6781	Approved
0.7423	Intermediate Similarity	NPD6777	Approved
0.7423	Intermediate Similarity	NPD6779	Approved
0.7423	Intermediate Similarity	NPD6776	Approved
0.7423	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6780	Approved
0.7423	Intermediate Similarity	NPD6778	Approved
0.7423	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD8313	Approved
0.7419	Intermediate Similarity	NPD8312	Approved
0.7414	Intermediate Similarity	NPD3226	Approved
0.7407	Intermediate Similarity	NPD4287	Approved
0.7394	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD37	Approved
0.7384	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2346	Discontinued
0.7381	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2799	Discontinued
0.7362	Intermediate Similarity	NPD3027	Phase 3
0.736	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD4966	Approved
0.736	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.7351	Intermediate Similarity	NPD5953	Discontinued
0.7348	Intermediate Similarity	NPD5711	Approved
0.7348	Intermediate Similarity	NPD5710	Approved
0.7348	Intermediate Similarity	NPD7229	Phase 3
0.7337	Intermediate Similarity	NPD7286	Phase 2
0.7321	Intermediate Similarity	NPD6099	Approved
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7321	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD2313	Discontinued
0.7313	Intermediate Similarity	NPD7783	Phase 2
0.7313	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7435	Discontinued
0.731	Intermediate Similarity	NPD6190	Approved
0.7302	Intermediate Similarity	NPD8150	Discontinued
0.7301	Intermediate Similarity	NPD4908	Phase 1
0.73	Intermediate Similarity	NPD8151	Discontinued
0.7283	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7549	Discontinued
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4363	Phase 3
0.7254	Intermediate Similarity	NPD4360	Phase 2
0.7251	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7907	Approved
0.7239	Intermediate Similarity	NPD9494	Approved
0.7233	Intermediate Similarity	NPD4665	Approved
0.7233	Intermediate Similarity	NPD4111	Phase 1
0.7222	Intermediate Similarity	NPD7698	Approved
0.7222	Intermediate Similarity	NPD7696	Phase 3
0.7222	Intermediate Similarity	NPD7697	Approved
0.7216	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2296	Approved
0.72	Intermediate Similarity	NPD7584	Approved
0.7191	Intermediate Similarity	NPD6844	Discontinued
0.7189	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1933	Approved
0.7172	Intermediate Similarity	NPD6823	Phase 2
0.7165	Intermediate Similarity	NPD6534	Approved
0.7165	Intermediate Similarity	NPD6535	Approved
0.7164	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7151	Intermediate Similarity	NPD5760	Phase 2
0.7151	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD6651	Approved
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD5242	Approved
0.7099	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6280	Approved
0.7095	Intermediate Similarity	NPD6279	Approved
0.7094	Intermediate Similarity	NPD7874	Approved
0.7094	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2403	Approved
0.7076	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD7801	Approved
0.7056	Intermediate Similarity	NPD7700	Phase 2
0.7056	Intermediate Similarity	NPD7699	Phase 2
0.7056	Intermediate Similarity	NPD8455	Phase 2
0.7037	Intermediate Similarity	NPD7240	Approved
0.7035	Intermediate Similarity	NPD2424	Discontinued
0.7035	Intermediate Similarity	NPD2493	Approved
0.7035	Intermediate Similarity	NPD2494	Approved
0.703	Intermediate Similarity	NPD2861	Phase 2
0.7022	Intermediate Similarity	NPD7458	Discontinued
0.7021	Intermediate Similarity	NPD1729	Discontinued
0.7018	Intermediate Similarity	NPD5405	Approved
0.7018	Intermediate Similarity	NPD5404	Approved
0.7018	Intermediate Similarity	NPD5406	Approved
0.7018	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD3764	Approved
0.7005	Intermediate Similarity	NPD2163	Approved
0.6989	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD1610	Phase 2
0.6975	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6808	Phase 2

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