NPASS Compound

Structure

NPC45257 OpenBabel07101719142D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.7469 -0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3457 -1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 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 -0.4067 2.5316 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 -3.7524 -0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 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 -1.5823 0.9135 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 0.9511 1.3090 0.0000 C 0 0 1 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 -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 0.9511 0.3090 0.0000 C 0 0 1 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 4.4152 -1.6910 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 -1.8080 3.5497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 18 2 0 0 0 0 10 25 1 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 10 1 6 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 13 1 6 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	363.042
LogP:	4.994
LogD:	3.453
LogS:	-3.685
# Rotatable Bonds:	3
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.808
Synthetic Accessibility Score:	3.661
Fsp3:	0.333
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:	-4.796
MDCK Permeability:	1.2974610399396624e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.248
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	96.21698760986328%
Volume Distribution (VD):	1.153
Pgp-substrate:	6.5896077156066895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.436
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.674
CYP2D6-substrate:	0.642
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.553

ADMET: Excretion

Clearance (CL):	11.164
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.503
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.937
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.416
Respiratory Toxicity:	0.697

Download Data

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

Natural Product: NPC45257

Natural Product ID:	NPC45257
*Common Name:**	Lespeflorin G7
IUPAC Name:	(6aR,11aR)-8-methoxy-10-(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:	Lespeflorin G7
Standard InCHIKey:	JZCLWJAANXMNAY-JXFKEZNVSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-11(2)4-6-14-19(23)18(24-3)9-15-16-10-25-17-8-12(22)5-7-13(17)20(16)26-21(14)15/h4-5,7-9,16,20,22-23H,6,10H2,1-3H3/t16-,20-/m0/s1
SMILES:	COc1cc2[C@@H]3COc4c([C@@H]3Oc2c(c1O)CC=C(C)C)ccc(c4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560103
PubChem CID:	25243162
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	=	6020.0	nM	PMID[465635]

☑ 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 NPC45257 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	460
0.1-0.2	1568
0.2-0.3	4341
0.3-0.4	12075
0.4-0.5	6301
0.5-0.6	4010
0.6-0.7	6454
0.7-0.8	5670
0.8-0.85	964
0.85-0.9	643
0.9-0.95	174
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC93323
1.0	High Similarity	NPC12641
1.0	High Similarity	NPC280092
0.9926	High Similarity	NPC85264
0.9926	High Similarity	NPC102044
0.9926	High Similarity	NPC47633
0.9854	High Similarity	NPC63879
0.9853	High Similarity	NPC107161
0.9784	High Similarity	NPC16269
0.9784	High Similarity	NPC21776
0.9779	High Similarity	NPC247291
0.9706	High Similarity	NPC309124
0.9706	High Similarity	NPC184797
0.9706	High Similarity	NPC259519
0.9706	High Similarity	NPC160283
0.9706	High Similarity	NPC254759
0.9706	High Similarity	NPC27495
0.9643	High Similarity	NPC101376
0.9635	High Similarity	NPC263261
0.9635	High Similarity	NPC471389
0.9635	High Similarity	NPC87725
0.9632	High Similarity	NPC473739
0.9632	High Similarity	NPC236306
0.9632	High Similarity	NPC260741
0.9632	High Similarity	NPC245207
0.9632	High Similarity	NPC232164
0.9632	High Similarity	NPC127218
0.9632	High Similarity	NPC319647
0.9632	High Similarity	NPC292882
0.9632	High Similarity	NPC25966
0.9632	High Similarity	NPC70682
0.9568	High Similarity	NPC50250
0.9559	High Similarity	NPC107551
0.9559	High Similarity	NPC102904
0.9559	High Similarity	NPC176051
0.9559	High Similarity	NPC276490
0.9559	High Similarity	NPC103976
0.9559	High Similarity	NPC474282
0.9559	High Similarity	NPC326797
0.9496	High Similarity	NPC477616
0.9493	High Similarity	NPC311530
0.9493	High Similarity	NPC35216
0.9489	High Similarity	NPC471388
0.9485	High Similarity	NPC162659
0.9485	High Similarity	NPC270456
0.9485	High Similarity	NPC265433
0.9485	High Similarity	NPC173660
0.9485	High Similarity	NPC248727
0.9444	High Similarity	NPC160196
0.9433	High Similarity	NPC260397
0.9429	High Similarity	NPC473108
0.9424	High Similarity	NPC2613
0.9424	High Similarity	NPC204347
0.9424	High Similarity	NPC59841
0.9424	High Similarity	NPC475891
0.9416	High Similarity	NPC477938
0.9412	High Similarity	NPC473413
0.9412	High Similarity	NPC112939
0.9412	High Similarity	NPC121812
0.9412	High Similarity	NPC94750
0.9412	High Similarity	NPC195022
0.9412	High Similarity	NPC134968
0.9412	High Similarity	NPC112246
0.9412	High Similarity	NPC470356
0.9412	High Similarity	NPC474206
0.9362	High Similarity	NPC469557
0.9362	High Similarity	NPC307466
0.9348	High Similarity	NPC32630
0.9343	High Similarity	NPC263367
0.9343	High Similarity	NPC470802
0.9343	High Similarity	NPC474639
0.9343	High Similarity	NPC230734
0.9343	High Similarity	NPC477939
0.9343	High Similarity	NPC16435
0.9343	High Similarity	NPC472336
0.9343	High Similarity	NPC29799
0.9343	High Similarity	NPC54743
0.9343	High Similarity	NPC156502
0.9343	High Similarity	NPC306441
0.9343	High Similarity	NPC177160
0.9343	High Similarity	NPC209985
0.9343	High Similarity	NPC472334
0.9343	High Similarity	NPC10737
0.9343	High Similarity	NPC227503
0.9338	High Similarity	NPC193026
0.9338	High Similarity	NPC474478
0.9338	High Similarity	NPC187616
0.9338	High Similarity	NPC49603
0.9338	High Similarity	NPC317380
0.9315	High Similarity	NPC159922
0.9315	High Similarity	NPC80918
0.9315	High Similarity	NPC188578
0.9301	High Similarity	NPC301961
0.9301	High Similarity	NPC71726
0.9301	High Similarity	NPC166584
0.9275	High Similarity	NPC211549
0.927	High Similarity	NPC260898
0.927	High Similarity	NPC234333
0.927	High Similarity	NPC61946
0.927	High Similarity	NPC472337
0.927	High Similarity	NPC47398
0.927	High Similarity	NPC151224
0.9265	High Similarity	NPC11060
0.9265	High Similarity	NPC158331
0.9225	High Similarity	NPC181615
0.922	High Similarity	NPC81638
0.9214	High Similarity	NPC265075
0.9203	High Similarity	NPC234952
0.9203	High Similarity	NPC269091
0.9203	High Similarity	NPC302701
0.9203	High Similarity	NPC78047
0.9197	High Similarity	NPC106215
0.9197	High Similarity	NPC478085
0.9197	High Similarity	NPC287745
0.9197	High Similarity	NPC124085
0.9197	High Similarity	NPC117048
0.9191	High Similarity	NPC202762
0.9191	High Similarity	NPC175067
0.9191	High Similarity	NPC127624
0.9191	High Similarity	NPC86655
0.9191	High Similarity	NPC204215
0.9191	High Similarity	NPC6451
0.9172	High Similarity	NPC472710
0.9172	High Similarity	NPC472709
0.9167	High Similarity	NPC473408
0.9167	High Similarity	NPC20757
0.9167	High Similarity	NPC227516
0.9161	High Similarity	NPC233980
0.9161	High Similarity	NPC226540
0.9161	High Similarity	NPC317053
0.9161	High Similarity	NPC324492
0.9149	High Similarity	NPC41782
0.9137	High Similarity	NPC474687
0.913	High Similarity	NPC99572
0.913	High Similarity	NPC126409
0.913	High Similarity	NPC256262
0.913	High Similarity	NPC164787
0.9124	High Similarity	NPC229442
0.9124	High Similarity	NPC85435
0.9124	High Similarity	NPC26394
0.9124	High Similarity	NPC475840
0.9124	High Similarity	NPC263064
0.9124	High Similarity	NPC168059
0.9118	High Similarity	NPC268917
0.9118	High Similarity	NPC236014
0.9118	High Similarity	NPC280653
0.9118	High Similarity	NPC150011
0.9118	High Similarity	NPC45715
0.9118	High Similarity	NPC474356
0.9118	High Similarity	NPC206224
0.9118	High Similarity	NPC129106
0.9118	High Similarity	NPC164574
0.9118	High Similarity	NPC118114
0.9118	High Similarity	NPC196765
0.9118	High Similarity	NPC300875
0.9118	High Similarity	NPC17343
0.9118	High Similarity	NPC12275
0.9118	High Similarity	NPC12875
0.9118	High Similarity	NPC207892
0.9118	High Similarity	NPC228369
0.9118	High Similarity	NPC476166
0.9118	High Similarity	NPC232275
0.9118	High Similarity	NPC129784
0.911	High Similarity	NPC2745
0.9103	High Similarity	NPC211561
0.9097	High Similarity	NPC320671
0.9097	High Similarity	NPC320970
0.9097	High Similarity	NPC328567
0.9097	High Similarity	NPC474397
0.9097	High Similarity	NPC327412
0.9091	High Similarity	NPC178014
0.9091	High Similarity	NPC42716
0.9091	High Similarity	NPC474749
0.9091	High Similarity	NPC11422
0.9091	High Similarity	NPC180953
0.9091	High Similarity	NPC221318
0.9085	High Similarity	NPC474104
0.9085	High Similarity	NPC258083
0.9078	High Similarity	NPC471414
0.9078	High Similarity	NPC178054
0.9071	High Similarity	NPC475836
0.9065	High Similarity	NPC18189
0.9065	High Similarity	NPC20829
0.9065	High Similarity	NPC262585
0.9065	High Similarity	NPC3049
0.9058	High Similarity	NPC16485
0.9058	High Similarity	NPC326095
0.9058	High Similarity	NPC310854
0.9058	High Similarity	NPC244983
0.9058	High Similarity	NPC170694
0.9051	High Similarity	NPC13005
0.9051	High Similarity	NPC126029
0.9051	High Similarity	NPC15658
0.9051	High Similarity	NPC78770
0.9051	High Similarity	NPC219876
0.9051	High Similarity	NPC253105
0.9051	High Similarity	NPC185604
0.9051	High Similarity	NPC61477
0.9051	High Similarity	NPC261619
0.9051	High Similarity	NPC230219

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 NPC45257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	890
0.2-0.3	1869
0.3-0.4	2764
0.4-0.5	1596
0.5-0.6	882
0.6-0.7	620
0.7-0.8	145
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9051	High Similarity	NPD1612	Clinical (unspecified phase)
0.9051	High Similarity	NPD1613	Approved
0.8897	High Similarity	NPD1529	Clinical (unspecified phase)
0.8832	High Similarity	NPD3027	Phase 3
0.8824	High Similarity	NPD1530	Clinical (unspecified phase)
0.8633	High Similarity	NPD4907	Clinical (unspecified phase)
0.8551	High Similarity	NPD2861	Phase 2
0.8489	Intermediate Similarity	NPD4908	Phase 1
0.8382	Intermediate Similarity	NPD1610	Phase 2
0.8312	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1934	Approved
0.8169	Intermediate Similarity	NPD4625	Phase 3
0.8165	Intermediate Similarity	NPD5494	Approved
0.8105	Intermediate Similarity	NPD1653	Approved
0.8101	Intermediate Similarity	NPD6234	Discontinued
0.8077	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD4749	Approved
0.7986	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7933	Intermediate Similarity	NPD6674	Discontinued
0.7933	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5844	Phase 1
0.7898	Intermediate Similarity	NPD37	Approved
0.7877	Intermediate Similarity	NPD4060	Phase 1
0.7866	Intermediate Similarity	NPD7228	Approved
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4966	Approved
0.7862	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD3882	Suspended
0.7853	Intermediate Similarity	NPD6166	Phase 2
0.7853	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3018	Phase 2
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.7758	Intermediate Similarity	NPD3818	Discontinued
0.7755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3620	Phase 2
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7683	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5588	Approved
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7622	Intermediate Similarity	NPD2983	Phase 2
0.7622	Intermediate Similarity	NPD2982	Phase 2
0.7613	Intermediate Similarity	NPD1511	Approved
0.7609	Intermediate Similarity	NPD6671	Approved
0.7605	Intermediate Similarity	NPD7054	Approved
0.76	Intermediate Similarity	NPD4536	Approved
0.76	Intermediate Similarity	NPD4538	Approved
0.76	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5124	Phase 1
0.7574	Intermediate Similarity	NPD228	Approved
0.7569	Intermediate Similarity	NPD6696	Suspended
0.7569	Intermediate Similarity	NPD8651	Approved
0.756	Intermediate Similarity	NPD7472	Approved
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7548	Intermediate Similarity	NPD5058	Phase 3
0.7547	Intermediate Similarity	NPD4380	Phase 2
0.7532	Intermediate Similarity	NPD6331	Phase 2
0.7529	Intermediate Similarity	NPD7549	Discontinued
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7483	Intermediate Similarity	NPD1091	Approved
0.7483	Intermediate Similarity	NPD3705	Approved
0.7471	Intermediate Similarity	NPD6559	Discontinued
0.7469	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3817	Phase 2
0.7466	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4663	Approved
0.7452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5960	Phase 3
0.7426	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD3021	Approved
0.7425	Intermediate Similarity	NPD2489	Approved
0.7425	Intermediate Similarity	NPD27	Approved
0.7414	Intermediate Similarity	NPD7906	Approved
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.741	Intermediate Similarity	NPD6232	Discontinued
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1465	Phase 2
0.7405	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1558	Phase 1
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7212	Phase 2
0.7389	Intermediate Similarity	NPD7213	Phase 3
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7384	Intermediate Similarity	NPD4577	Approved
0.7384	Intermediate Similarity	NPD4578	Approved
0.7384	Intermediate Similarity	NPD7313	Approved
0.7384	Intermediate Similarity	NPD7310	Approved
0.7384	Intermediate Similarity	NPD7312	Approved
0.7384	Intermediate Similarity	NPD7311	Approved
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD7240	Approved
0.7365	Intermediate Similarity	NPD2969	Approved
0.7365	Intermediate Similarity	NPD2970	Approved
0.7362	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5177	Phase 3
0.7355	Intermediate Similarity	NPD1652	Phase 2
0.7351	Intermediate Similarity	NPD5735	Approved
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD7447	Phase 1
0.7341	Intermediate Similarity	NPD7309	Approved
0.7338	Intermediate Similarity	NPD5762	Approved
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5763	Approved
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4675	Approved
0.7329	Intermediate Similarity	NPD4678	Approved
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.732	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3892	Phase 2
0.7308	Intermediate Similarity	NPD7466	Approved
0.7308	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD3051	Approved
0.7301	Intermediate Similarity	NPD7819	Suspended
0.7301	Intermediate Similarity	NPD5929	Approved
0.729	Intermediate Similarity	NPD1549	Phase 2
0.729	Intermediate Similarity	NPD2424	Discontinued
0.7273	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7246	Intermediate Similarity	NPD1247	Approved
0.7241	Intermediate Similarity	NPD422	Phase 1
0.7241	Intermediate Similarity	NPD8054	Approved
0.7241	Intermediate Similarity	NPD8053	Approved
0.7234	Intermediate Similarity	NPD7157	Approved
0.7233	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3540	Phase 1
0.7226	Intermediate Similarity	NPD2684	Approved
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7206	Intermediate Similarity	NPD968	Approved
0.7197	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4110	Phase 3
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7340	Approved
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3539	Phase 1
0.7161	Intermediate Similarity	NPD2935	Discontinued
0.716	Intermediate Similarity	NPD4005	Discontinued
0.7153	Intermediate Similarity	NPD290	Approved
0.7153	Intermediate Similarity	NPD1357	Approved
0.7152	Intermediate Similarity	NPD2560	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD2563	Approved
0.7152	Intermediate Similarity	NPD2677	Approved
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3384	Approved
0.7134	Intermediate Similarity	NPD3382	Approved
0.7134	Intermediate Similarity	NPD4237	Approved
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7134	Intermediate Similarity	NPD4236	Phase 3
0.7134	Intermediate Similarity	NPD3383	Approved
0.7125	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6002	Phase 3
0.7115	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6004	Phase 3
0.7115	Intermediate Similarity	NPD1375	Discontinued
0.7115	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6005	Phase 3
0.7114	Intermediate Similarity	NPD6584	Phase 3
0.7108	Intermediate Similarity	NPD7768	Phase 2
0.7107	Intermediate Similarity	NPD7124	Phase 2
0.7103	Intermediate Similarity	NPD5126	Approved
0.7103	Intermediate Similarity	NPD5125	Phase 3
0.7101	Intermediate Similarity	NPD6071	Discontinued
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7092	Intermediate Similarity	NPD1398	Phase 1
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD3750	Approved
0.7089	Intermediate Similarity	NPD4535	Phase 3
0.7086	Intermediate Similarity	NPD7095	Approved
0.7078	Intermediate Similarity	NPD4097	Suspended
0.7073	Intermediate Similarity	NPD6072	Discontinued
0.7073	Intermediate Similarity	NPD7411	Suspended
0.7063	Intermediate Similarity	NPD7041	Phase 2
0.7063	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD4140	Approved
0.7059	Intermediate Similarity	NPD2238	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