NPASS Compound

Structure

CID63879 OpenBabel06191715402D 33 36 0 0 1 0 0 0 0 0999 V2000 2.5188 4.5013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7585 4.5017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6806 3.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2763 2.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0043 -0.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7992 2.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6383 2.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0297 1.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5182 2.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6780 0.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 -1.9377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3565 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 -1.9384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6385 3.9933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3289 2.6100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5180 1.4524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6782 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8391 -1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 -1.4538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3567 0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5174 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5175 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6787 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6790 0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 -0.4845 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2370 1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3851 -1.9539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3560 0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7990 1.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5173 -1.4541 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 32 1 0 0 0 0 16 20 1 0 0 0 0 16 26 2 0 0 0 0 17 24 2 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 13 1 1 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 25 2 0 0 0 0 21 29 1 0 0 0 0 22 23 2 0 0 0 0 22 32 1 0 0 0 0 23 26 1 0 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 23 1 1 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.22
Volume:	472.972
LogP:	7.349
LogD:	4.261
LogS:	-2.756
# Rotatable Bonds:	6
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.544
Synthetic Accessibility Score:	4.172
Fsp3:	0.407
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.912
MDCK Permeability:	1.411330231348984e-05
Pgp-inhibitor:	0.876
Pgp-substrate:	0.542
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	84.44751739501953%
Volume Distribution (VD):	2.65
Pgp-substrate:	21.039756774902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	0.338
CYP3A4-substrate:	0.642

ADMET: Excretion

Clearance (CL):	9.34
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.897
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.688
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC63879

Natural Product ID:	NPC63879
*Common Name:**	Lespeflorin G3
IUPAC Name:	(6aR,11aR)-1,9-dimethoxy-2,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,8-diol
Synonyms:	Lespeflorin G3
Standard InCHIKey:	HZCGTSDDHHPRDX-UZTOHYMASA-N
Standard InCHI:	InChI=1S/C27H32O6/c1-14(2)7-9-16-20(28)12-22-23(26(16)31-6)27-19(13-32-22)18-11-21(29)25(30-5)17(24(18)33-27)10-8-15(3)4/h7-8,11-12,19,27-29H,9-10,13H2,1-6H3/t19-,27+/m0/s1
SMILES:	COc1c(CC=C(C)C)c(O)cc2c1[C@@H]1Oc3c([C@@H]1CO2)cc(c(c3CC=C(C)C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555351
PubChem CID:	25242995
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	=	2030.0	nM	PMID[530483]

☑ 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 NPC63879 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	456
0.1-0.2	1591
0.2-0.3	4418
0.3-0.4	12059
0.4-0.5	6367
0.5-0.6	4121
0.6-0.7	6469
0.7-0.8	5507
0.8-0.85	954
0.85-0.9	562
0.9-0.95	171
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC85264
0.9926	High Similarity	NPC102044
0.9926	High Similarity	NPC47633
0.9854	High Similarity	NPC93323
0.9854	High Similarity	NPC280092
0.9854	High Similarity	NPC45257
0.9854	High Similarity	NPC12641
0.9779	High Similarity	NPC247291
0.9708	High Similarity	NPC107161
0.9706	High Similarity	NPC259519
0.9643	High Similarity	NPC16269
0.9643	High Similarity	NPC101376
0.9643	High Similarity	NPC21776
0.9568	High Similarity	NPC50250
0.9562	High Similarity	NPC184797
0.9562	High Similarity	NPC160283
0.9562	High Similarity	NPC254759
0.9562	High Similarity	NPC27495
0.9562	High Similarity	NPC309124
0.9493	High Similarity	NPC311530
0.9493	High Similarity	NPC471389
0.9493	High Similarity	NPC263261
0.9493	High Similarity	NPC87725
0.9489	High Similarity	NPC232164
0.9489	High Similarity	NPC473739
0.9489	High Similarity	NPC127218
0.9489	High Similarity	NPC25966
0.9489	High Similarity	NPC236306
0.9489	High Similarity	NPC319647
0.9489	High Similarity	NPC70682
0.9489	High Similarity	NPC245207
0.9489	High Similarity	NPC292882
0.9489	High Similarity	NPC260741
0.9444	High Similarity	NPC160196
0.9433	High Similarity	NPC260397
0.9416	High Similarity	NPC176051
0.9416	High Similarity	NPC102904
0.9416	High Similarity	NPC103976
0.9416	High Similarity	NPC107551
0.9416	High Similarity	NPC326797
0.9416	High Similarity	NPC276490
0.9416	High Similarity	NPC474282
0.9362	High Similarity	NPC307466
0.9357	High Similarity	NPC477616
0.9353	High Similarity	NPC35216
0.9348	High Similarity	NPC471388
0.9343	High Similarity	NPC470802
0.9343	High Similarity	NPC162659
0.9343	High Similarity	NPC173660
0.9343	High Similarity	NPC265433
0.9343	High Similarity	NPC248727
0.9343	High Similarity	NPC270456
0.9315	High Similarity	NPC80918
0.9315	High Similarity	NPC188578
0.9306	High Similarity	NPC472710
0.9306	High Similarity	NPC472709
0.9301	High Similarity	NPC71726
0.9291	High Similarity	NPC473108
0.9286	High Similarity	NPC475891
0.9286	High Similarity	NPC204347
0.9286	High Similarity	NPC2613
0.9286	High Similarity	NPC59841
0.9275	High Similarity	NPC477938
0.927	High Similarity	NPC473413
0.927	High Similarity	NPC112939
0.927	High Similarity	NPC260898
0.927	High Similarity	NPC112246
0.927	High Similarity	NPC474206
0.927	High Similarity	NPC195022
0.927	High Similarity	NPC470356
0.927	High Similarity	NPC234333
0.927	High Similarity	NPC134968
0.927	High Similarity	NPC94750
0.927	High Similarity	NPC47398
0.927	High Similarity	NPC121812
0.9225	High Similarity	NPC469557
0.9225	High Similarity	NPC181615
0.9209	High Similarity	NPC32630
0.9203	High Similarity	NPC16435
0.9203	High Similarity	NPC29799
0.9203	High Similarity	NPC227503
0.9203	High Similarity	NPC263367
0.9203	High Similarity	NPC474639
0.9203	High Similarity	NPC10737
0.9203	High Similarity	NPC472334
0.9203	High Similarity	NPC177160
0.9203	High Similarity	NPC209985
0.9203	High Similarity	NPC477939
0.9203	High Similarity	NPC472336
0.9203	High Similarity	NPC54743
0.9203	High Similarity	NPC156502
0.9203	High Similarity	NPC230734
0.9203	High Similarity	NPC306441
0.9197	High Similarity	NPC474478
0.9197	High Similarity	NPC49603
0.9197	High Similarity	NPC187616
0.9197	High Similarity	NPC317380
0.9197	High Similarity	NPC193026
0.9191	High Similarity	NPC175067
0.9191	High Similarity	NPC127624
0.9191	High Similarity	NPC204215
0.9184	High Similarity	NPC159922
0.9167	High Similarity	NPC166584
0.9167	High Similarity	NPC301961
0.9161	High Similarity	NPC226540
0.9161	High Similarity	NPC317053
0.9161	High Similarity	NPC324492
0.9137	High Similarity	NPC211549
0.913	High Similarity	NPC61946
0.913	High Similarity	NPC472337
0.913	High Similarity	NPC151224
0.9124	High Similarity	NPC11060
0.9124	High Similarity	NPC158331
0.9118	High Similarity	NPC271945
0.9118	High Similarity	NPC181497
0.911	High Similarity	NPC2745
0.9097	High Similarity	NPC320970
0.9097	High Similarity	NPC320671
0.9097	High Similarity	NPC328567
0.9097	High Similarity	NPC327412
0.9091	High Similarity	NPC90645
0.9085	High Similarity	NPC81638
0.9085	High Similarity	NPC474104
0.9078	High Similarity	NPC265075
0.9065	High Similarity	NPC78047
0.9065	High Similarity	NPC269091
0.9065	High Similarity	NPC302701
0.9065	High Similarity	NPC234952
0.9058	High Similarity	NPC326095
0.9058	High Similarity	NPC124085
0.9058	High Similarity	NPC106215
0.9058	High Similarity	NPC117048
0.9058	High Similarity	NPC287745
0.9058	High Similarity	NPC16485
0.9058	High Similarity	NPC244983
0.9058	High Similarity	NPC478085
0.9051	High Similarity	NPC86655
0.9051	High Similarity	NPC6451
0.9051	High Similarity	NPC202762
0.9048	High Similarity	NPC157783
0.9044	High Similarity	NPC237169
0.9044	High Similarity	NPC470624
0.9044	High Similarity	NPC470225
0.9044	High Similarity	NPC214860
0.9044	High Similarity	NPC27187
0.9041	High Similarity	NPC477612
0.9041	High Similarity	NPC195561
0.9041	High Similarity	NPC158784
0.9034	High Similarity	NPC20757
0.9034	High Similarity	NPC473876
0.9034	High Similarity	NPC227516
0.9034	High Similarity	NPC473408
0.9034	High Similarity	NPC270751
0.9028	High Similarity	NPC233980
0.9028	High Similarity	NPC112251
0.9021	High Similarity	NPC471415
0.9021	High Similarity	NPC470097
0.9021	High Similarity	NPC114119
0.9021	High Similarity	NPC473845
0.9014	High Similarity	NPC41782
0.9007	High Similarity	NPC291101
0.9007	High Similarity	NPC266197
0.9	High Similarity	NPC474687
0.8993	High Similarity	NPC141765
0.8993	High Similarity	NPC164787
0.8993	High Similarity	NPC126409
0.8993	High Similarity	NPC256262
0.8993	High Similarity	NPC24490
0.8993	High Similarity	NPC99572
0.8993	High Similarity	NPC165155
0.8993	High Similarity	NPC34103
0.8986	High Similarity	NPC229442
0.8986	High Similarity	NPC85435
0.8986	High Similarity	NPC470769
0.8986	High Similarity	NPC105554
0.8986	High Similarity	NPC263064
0.8986	High Similarity	NPC168059
0.8986	High Similarity	NPC475840
0.8986	High Similarity	NPC26394
0.898	High Similarity	NPC302915
0.8978	High Similarity	NPC12875
0.8978	High Similarity	NPC17343
0.8978	High Similarity	NPC164574
0.8978	High Similarity	NPC300875
0.8978	High Similarity	NPC280653
0.8978	High Similarity	NPC268266
0.8978	High Similarity	NPC150011
0.8978	High Similarity	NPC268342
0.8978	High Similarity	NPC309787
0.8978	High Similarity	NPC45715
0.8978	High Similarity	NPC232275
0.8978	High Similarity	NPC220825
0.8978	High Similarity	NPC236014
0.8978	High Similarity	NPC129784
0.8978	High Similarity	NPC474356
0.8978	High Similarity	NPC196765
0.8978	High Similarity	NPC268917
0.8978	High Similarity	NPC42760
0.8978	High Similarity	NPC206224
0.8978	High Similarity	NPC228369

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 NPC63879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	915
0.2-0.3	1932
0.3-0.4	2753
0.4-0.5	1584
0.5-0.6	869
0.6-0.7	588
0.7-0.8	128
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
0.8913	High Similarity	NPD1613	Approved
0.8913	High Similarity	NPD1612	Clinical (unspecified phase)
0.8824	High Similarity	NPD1530	Clinical (unspecified phase)
0.8759	High Similarity	NPD1529	Clinical (unspecified phase)
0.8696	High Similarity	NPD3027	Phase 3
0.85	High Similarity	NPD4907	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD2861	Phase 2
0.8357	Intermediate Similarity	NPD4908	Phase 1
0.8248	Intermediate Similarity	NPD1610	Phase 2
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1934	Approved
0.8112	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6234	Discontinued
0.8054	Intermediate Similarity	NPD6674	Discontinued
0.805	Intermediate Similarity	NPD5494	Approved
0.8042	Intermediate Similarity	NPD4625	Phase 3
0.8	Intermediate Similarity	NPD4749	Approved
0.7987	Intermediate Similarity	NPD1653	Approved
0.7975	Intermediate Similarity	NPD7228	Approved
0.7962	Intermediate Similarity	NPD2801	Approved
0.7898	Intermediate Similarity	NPD37	Approved
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD4966	Approved
0.7862	Intermediate Similarity	NPD4965	Approved
0.7826	Intermediate Similarity	NPD1548	Phase 1
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4060	Phase 1
0.7755	Intermediate Similarity	NPD3620	Phase 2
0.775	Intermediate Similarity	NPD3882	Suspended
0.7744	Intermediate Similarity	NPD6166	Phase 2
0.7744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6696	Suspended
0.7669	Intermediate Similarity	NPD7199	Phase 2
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7655	Intermediate Similarity	NPD3018	Phase 2
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7609	Intermediate Similarity	NPD6671	Approved
0.7605	Intermediate Similarity	NPD7054	Approved
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7586	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8651	Approved
0.756	Intermediate Similarity	NPD7472	Approved
0.755	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD2982	Phase 2
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7484	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7483	Intermediate Similarity	NPD3705	Approved
0.7471	Intermediate Similarity	NPD7240	Approved
0.7469	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5124	Phase 1
0.7445	Intermediate Similarity	NPD228	Approved
0.7438	Intermediate Similarity	NPD4380	Phase 2
0.7436	Intermediate Similarity	NPD5058	Phase 3
0.7431	Intermediate Similarity	NPD2981	Phase 2
0.7427	Intermediate Similarity	NPD7549	Discontinued
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6331	Phase 2
0.7419	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7906	Approved
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1465	Phase 2
0.7405	Intermediate Similarity	NPD1512	Approved
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7313	Approved
0.7384	Intermediate Similarity	NPD7312	Approved
0.7384	Intermediate Similarity	NPD7310	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	NPD3600	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6559	Discontinued
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7361	Intermediate Similarity	NPD1091	Approved
0.7356	Intermediate Similarity	NPD4663	Approved
0.7351	Intermediate Similarity	NPD5735	Approved
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7447	Phase 1
0.7341	Intermediate Similarity	NPD7309	Approved
0.7338	Intermediate Similarity	NPD5762	Approved
0.7338	Intermediate Similarity	NPD5763	Approved
0.7338	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7321	Intermediate Similarity	NPD27	Approved
0.7321	Intermediate Similarity	NPD2489	Approved
0.732	Intermediate Similarity	NPD5960	Phase 3
0.731	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7466	Approved
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD7340	Approved
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7301	Intermediate Similarity	NPD7819	Suspended
0.7299	Intermediate Similarity	NPD3021	Approved
0.7299	Intermediate Similarity	NPD3022	Approved
0.7296	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1558	Phase 1
0.7283	Intermediate Similarity	NPD4578	Approved
0.7283	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD7213	Phase 3
0.7278	Intermediate Similarity	NPD7212	Phase 2
0.7273	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2970	Approved
0.7262	Intermediate Similarity	NPD2969	Approved
0.7261	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD5177	Phase 3
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD8054	Approved
0.7241	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8053	Approved
0.7234	Intermediate Similarity	NPD7157	Approved
0.7226	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4678	Approved
0.7222	Intermediate Similarity	NPD4675	Approved
0.7208	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3051	Approved
0.7197	Intermediate Similarity	NPD3892	Phase 2
0.7195	Intermediate Similarity	NPD5929	Approved
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2424	Discontinued
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7169	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1247	Approved
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7115	Intermediate Similarity	NPD3540	Phase 1
0.7108	Intermediate Similarity	NPD7768	Phase 2
0.7107	Intermediate Similarity	NPD7124	Phase 2
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD6071	Discontinued
0.7101	Intermediate Similarity	NPD2684	Approved
0.7092	Intermediate Similarity	NPD1398	Phase 1
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7086	Intermediate Similarity	NPD7095	Approved
0.7081	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD968	Approved
0.7073	Intermediate Similarity	NPD6072	Discontinued
0.7063	Intermediate Similarity	NPD7041	Phase 2
0.7063	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2935	Discontinued
0.7051	Intermediate Similarity	NPD3539	Phase 1
0.705	Intermediate Similarity	NPD4750	Phase 3
0.7048	Intermediate Similarity	NPD2560	Approved
0.7048	Intermediate Similarity	NPD2563	Approved
0.7048	Intermediate Similarity	NPD5402	Approved
0.7044	Intermediate Similarity	NPD2677	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7034	Intermediate Similarity	NPD1357	Approved
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7032	Intermediate Similarity	NPD6111	Discontinued
0.703	Intermediate Similarity	NPD6801	Discontinued
0.703	Intermediate Similarity	NPD3382	Approved
0.703	Intermediate Similarity	NPD3384	Approved
0.703	Intermediate Similarity	NPD3383	Approved
0.7029	Intermediate Similarity	NPD290	Approved
0.7025	Intermediate Similarity	NPD4236	Phase 3
0.7025	Intermediate Similarity	NPD4237	Approved
0.7019	Intermediate Similarity	NPD2532	Approved
0.7019	Intermediate Similarity	NPD2534	Approved
0.7019	Intermediate Similarity	NPD2533	Approved
0.7019	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3657	Discovery
0.7006	Intermediate Similarity	NPD1375	Discontinued
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD3787	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