NPASS Compound

Structure

NPC102044 OpenBabel07101719242D 26 29 0 0 1 0 0 0 0 0999 V2000 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0850 3.1910 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 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 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 0.4067 -2.5316 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 1.5823 -0.9135 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 -0.9511 2.6910 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 0.0000 -1.6180 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 -0.9511 -1.3090 0.0000 C 0 0 1 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 1.9890 -1.8271 0.0000 C 0 0 0 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 0.5878 -0.8090 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 -0.9511 -0.3090 0.0000 C 0 0 1 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 5 1 0 0 0 0 4 11 2 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 16 2 0 0 0 0 8 18 1 0 0 0 0 9 17 1 0 0 0 0 9 19 2 0 0 0 0 10 25 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 15 10 1 6 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 21 14 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	363.042
LogP:	5.036
LogD:	3.694
LogS:	-4.046
# 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:	3.641
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:	-4.828
MDCK Permeability:	1.1481900401122402e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.555
30% Bioavailability (F30%):	0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	96.48275756835938%
Volume Distribution (VD):	0.973
Pgp-substrate:	5.774430751800537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.566
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.875
CYP2C19-substrate:	0.441
CYP2C9-inhibitor:	0.887
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.787
CYP2D6-substrate:	0.827
CYP3A4-inhibitor:	0.613
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	13.15
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.475
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.886
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.783
Respiratory Toxicity:	0.636

Download Data

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

Natural Product: NPC102044

Natural Product ID:	NPC102044
*Common Name:**	Eryvarin K
IUPAC Name:	(6aR,11aR)-8-methoxy-2-(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
Synonyms:	Eryvarin K
Standard InCHIKey:	CVUYVQZALVRDIK-BTYIYWSLSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-11(2)4-5-12-6-14-18(8-16(12)22)25-10-15-13-7-20(24-3)17(23)9-19(13)26-21(14)15/h4,6-9,15,21-23H,5,10H2,1-3H3/t15-,21-/m0/s1
SMILES:	CC(=CCc1cc2c(cc1O)OC[C@H]1c3cc(c(cc3O[C@@H]21)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079408
PubChem CID:	11187348
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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	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	5

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[456054]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[456054]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[456054]

☑ 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 NPC102044 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
1.0	High Similarity	NPC47633
1.0	High Similarity	NPC85264
0.9926	High Similarity	NPC93323
0.9926	High Similarity	NPC280092
0.9926	High Similarity	NPC63879
0.9926	High Similarity	NPC45257
0.9926	High Similarity	NPC12641
0.9852	High Similarity	NPC247291
0.9779	High Similarity	NPC107161
0.9778	High Similarity	NPC259519
0.9712	High Similarity	NPC101376
0.9712	High Similarity	NPC21776
0.9712	High Similarity	NPC16269
0.9632	High Similarity	NPC254759
0.9632	High Similarity	NPC27495
0.9632	High Similarity	NPC160283
0.9632	High Similarity	NPC309124
0.9632	High Similarity	NPC184797
0.9562	High Similarity	NPC87725
0.9562	High Similarity	NPC311530
0.9562	High Similarity	NPC263261
0.9562	High Similarity	NPC471389
0.9559	High Similarity	NPC319647
0.9559	High Similarity	NPC236306
0.9559	High Similarity	NPC70682
0.9559	High Similarity	NPC245207
0.9559	High Similarity	NPC473739
0.9559	High Similarity	NPC292882
0.9559	High Similarity	NPC232164
0.9559	High Similarity	NPC25966
0.9559	High Similarity	NPC127218
0.9559	High Similarity	NPC260741
0.9496	High Similarity	NPC50250
0.9485	High Similarity	NPC102904
0.9485	High Similarity	NPC107551
0.9485	High Similarity	NPC326797
0.9485	High Similarity	NPC474282
0.9485	High Similarity	NPC176051
0.9485	High Similarity	NPC276490
0.9485	High Similarity	NPC103976
0.9429	High Similarity	NPC307466
0.9424	High Similarity	NPC477616
0.942	High Similarity	NPC35216
0.9416	High Similarity	NPC471388
0.9412	High Similarity	NPC248727
0.9412	High Similarity	NPC173660
0.9412	High Similarity	NPC265433
0.9412	High Similarity	NPC470802
0.9412	High Similarity	NPC270456
0.9412	High Similarity	NPC162659
0.9375	High Similarity	NPC160196
0.9366	High Similarity	NPC71726
0.9362	High Similarity	NPC260397
0.9357	High Similarity	NPC473108
0.9353	High Similarity	NPC204347
0.9353	High Similarity	NPC2613
0.9353	High Similarity	NPC59841
0.9353	High Similarity	NPC475891
0.9343	High Similarity	NPC477938
0.9338	High Similarity	NPC234333
0.9338	High Similarity	NPC121812
0.9338	High Similarity	NPC134968
0.9338	High Similarity	NPC112246
0.9338	High Similarity	NPC112939
0.9338	High Similarity	NPC47398
0.9338	High Similarity	NPC260898
0.9338	High Similarity	NPC94750
0.9338	High Similarity	NPC473413
0.9338	High Similarity	NPC474206
0.9338	High Similarity	NPC470356
0.9338	High Similarity	NPC195022
0.9291	High Similarity	NPC469557
0.9275	High Similarity	NPC32630
0.927	High Similarity	NPC230734
0.927	High Similarity	NPC227503
0.927	High Similarity	NPC29799
0.927	High Similarity	NPC472336
0.927	High Similarity	NPC10737
0.927	High Similarity	NPC177160
0.927	High Similarity	NPC263367
0.927	High Similarity	NPC474639
0.927	High Similarity	NPC477939
0.927	High Similarity	NPC156502
0.927	High Similarity	NPC54743
0.927	High Similarity	NPC16435
0.927	High Similarity	NPC209985
0.927	High Similarity	NPC306441
0.927	High Similarity	NPC472334
0.9265	High Similarity	NPC193026
0.9265	High Similarity	NPC187616
0.9265	High Similarity	NPC49603
0.9265	High Similarity	NPC317380
0.9265	High Similarity	NPC474478
0.9259	High Similarity	NPC204215
0.9259	High Similarity	NPC127624
0.9259	High Similarity	NPC175067
0.9247	High Similarity	NPC188578
0.9247	High Similarity	NPC80918
0.9247	High Similarity	NPC159922
0.9236	High Similarity	NPC472709
0.9236	High Similarity	NPC472710
0.9231	High Similarity	NPC301961
0.9231	High Similarity	NPC166584
0.9225	High Similarity	NPC226540
0.9203	High Similarity	NPC211549
0.9197	High Similarity	NPC151224
0.9197	High Similarity	NPC61946
0.9197	High Similarity	NPC472337
0.9191	High Similarity	NPC11060
0.9191	High Similarity	NPC158331
0.9155	High Similarity	NPC181615
0.9149	High Similarity	NPC81638
0.9143	High Similarity	NPC265075
0.913	High Similarity	NPC78047
0.913	High Similarity	NPC234952
0.913	High Similarity	NPC302701
0.913	High Similarity	NPC269091
0.9124	High Similarity	NPC124085
0.9124	High Similarity	NPC287745
0.9124	High Similarity	NPC16485
0.9124	High Similarity	NPC478085
0.9124	High Similarity	NPC117048
0.9124	High Similarity	NPC106215
0.9124	High Similarity	NPC244983
0.9124	High Similarity	NPC326095
0.9118	High Similarity	NPC6451
0.9118	High Similarity	NPC202762
0.9118	High Similarity	NPC86655
0.9111	High Similarity	NPC214860
0.9111	High Similarity	NPC27187
0.9111	High Similarity	NPC470225
0.9097	High Similarity	NPC20757
0.9097	High Similarity	NPC473408
0.9097	High Similarity	NPC227516
0.9091	High Similarity	NPC112251
0.9091	High Similarity	NPC324492
0.9091	High Similarity	NPC233980
0.9091	High Similarity	NPC317053
0.9078	High Similarity	NPC41782
0.9065	High Similarity	NPC474687
0.9058	High Similarity	NPC256262
0.9058	High Similarity	NPC34103
0.9058	High Similarity	NPC164787
0.9058	High Similarity	NPC165155
0.9058	High Similarity	NPC99572
0.9058	High Similarity	NPC126409
0.9058	High Similarity	NPC141765
0.9058	High Similarity	NPC24490
0.9051	High Similarity	NPC475840
0.9051	High Similarity	NPC105554
0.9051	High Similarity	NPC26394
0.9051	High Similarity	NPC85435
0.9051	High Similarity	NPC263064
0.9051	High Similarity	NPC168059
0.9051	High Similarity	NPC229442
0.9044	High Similarity	NPC280653
0.9044	High Similarity	NPC476166
0.9044	High Similarity	NPC164574
0.9044	High Similarity	NPC300875
0.9044	High Similarity	NPC12275
0.9044	High Similarity	NPC220825
0.9044	High Similarity	NPC12875
0.9044	High Similarity	NPC17343
0.9044	High Similarity	NPC181497
0.9044	High Similarity	NPC42760
0.9044	High Similarity	NPC268342
0.9044	High Similarity	NPC45715
0.9044	High Similarity	NPC118114
0.9044	High Similarity	NPC268266
0.9044	High Similarity	NPC129106
0.9044	High Similarity	NPC150011
0.9044	High Similarity	NPC129784
0.9044	High Similarity	NPC196765
0.9044	High Similarity	NPC268917
0.9044	High Similarity	NPC236014
0.9044	High Similarity	NPC474356
0.9044	High Similarity	NPC207892
0.9044	High Similarity	NPC206224
0.9044	High Similarity	NPC228369
0.9044	High Similarity	NPC271945
0.9044	High Similarity	NPC232275
0.9041	High Similarity	NPC2745
0.9037	High Similarity	NPC45824
0.9034	High Similarity	NPC240521
0.9034	High Similarity	NPC211561
0.9028	High Similarity	NPC474397
0.9028	High Similarity	NPC327412
0.9028	High Similarity	NPC328567
0.9028	High Similarity	NPC320970
0.9028	High Similarity	NPC320671
0.9021	High Similarity	NPC221318
0.9021	High Similarity	NPC472457
0.9021	High Similarity	NPC90645
0.9021	High Similarity	NPC474749
0.9021	High Similarity	NPC178014
0.9021	High Similarity	NPC11422
0.9021	High Similarity	NPC42716
0.9021	High Similarity	NPC180953
0.9014	High Similarity	NPC258083
0.9014	High Similarity	NPC474104

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 NPC102044 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
0.8978	High Similarity	NPD1612	Clinical (unspecified phase)
0.8978	High Similarity	NPD1613	Approved
0.8889	High Similarity	NPD1530	Clinical (unspecified phase)
0.8824	High Similarity	NPD1529	Clinical (unspecified phase)
0.8759	High Similarity	NPD3027	Phase 3
0.8561	High Similarity	NPD4907	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD2861	Phase 2
0.8417	Intermediate Similarity	NPD4908	Phase 1
0.8309	Intermediate Similarity	NPD1610	Phase 2
0.8247	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1934	Approved
0.8153	Intermediate Similarity	NPD6234	Discontinued
0.8101	Intermediate Similarity	NPD5494	Approved
0.8099	Intermediate Similarity	NPD4625	Phase 3
0.8058	Intermediate Similarity	NPD4749	Approved
0.8042	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1653	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD6674	Discontinued
0.7949	Intermediate Similarity	NPD37	Approved
0.7914	Intermediate Similarity	NPD7228	Approved
0.7911	Intermediate Similarity	NPD4967	Phase 2
0.7911	Intermediate Similarity	NPD4966	Approved
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4965	Approved
0.7883	Intermediate Similarity	NPD1548	Phase 1
0.7867	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7808	Intermediate Similarity	NPD4060	Phase 1
0.7808	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3620	Phase 2
0.7799	Intermediate Similarity	NPD3882	Suspended
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7199	Phase 2
0.7708	Intermediate Similarity	NPD3018	Phase 2
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD5283	Phase 1
0.7622	Intermediate Similarity	NPD6696	Suspended
0.7622	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7074	Phase 3
0.76	Intermediate Similarity	NPD5588	Approved
0.7552	Intermediate Similarity	NPD2983	Phase 2
0.7552	Intermediate Similarity	NPD2982	Phase 2
0.7548	Intermediate Similarity	NPD1511	Approved
0.7545	Intermediate Similarity	NPD7054	Approved
0.7536	Intermediate Similarity	NPD6671	Approved
0.7535	Intermediate Similarity	NPD3705	Approved
0.7533	Intermediate Similarity	NPD4536	Approved
0.7533	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4538	Approved
0.7517	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5124	Phase 1
0.7517	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD5058	Phase 3
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7483	Intermediate Similarity	NPD2981	Phase 2
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7549	Discontinued
0.7468	Intermediate Similarity	NPD6331	Phase 2
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.7452	Intermediate Similarity	NPD1512	Approved
0.7434	Intermediate Similarity	NPD6100	Approved
0.7434	Intermediate Similarity	NPD6099	Approved
0.7431	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7075	Discontinued
0.7421	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1091	Approved
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7412	Intermediate Similarity	NPD7240	Approved
0.7407	Intermediate Similarity	NPD3817	Phase 2
0.7407	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4663	Approved
0.7389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5960	Phase 3
0.7365	Intermediate Similarity	NPD27	Approved
0.7365	Intermediate Similarity	NPD2489	Approved
0.7356	Intermediate Similarity	NPD7906	Approved
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD3022	Approved
0.7353	Intermediate Similarity	NPD6797	Phase 2
0.7353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6232	Discontinued
0.7346	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1558	Phase 1
0.7329	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7310	Approved
0.7326	Intermediate Similarity	NPD7312	Approved
0.7326	Intermediate Similarity	NPD7311	Approved
0.7326	Intermediate Similarity	NPD4577	Approved
0.7326	Intermediate Similarity	NPD7313	Approved
0.7326	Intermediate Similarity	NPD4578	Approved
0.7325	Intermediate Similarity	NPD7213	Phase 3
0.7325	Intermediate Similarity	NPD7212	Phase 2
0.7321	Intermediate Similarity	NPD7473	Discontinued
0.7315	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7251	Discontinued
0.731	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2970	Approved
0.7305	Intermediate Similarity	NPD2969	Approved
0.729	Intermediate Similarity	NPD5177	Phase 3
0.729	Intermediate Similarity	NPD1652	Phase 2
0.7289	Intermediate Similarity	NPD6959	Discontinued
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD5735	Approved
0.7283	Intermediate Similarity	NPD7309	Approved
0.7278	Intermediate Similarity	NPD7447	Phase 1
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD4675	Approved
0.7267	Intermediate Similarity	NPD4678	Approved
0.7267	Intermediate Similarity	NPD7808	Phase 3
0.7255	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3051	Approved
0.7246	Intermediate Similarity	NPD7229	Phase 3
0.7244	Intermediate Similarity	NPD7466	Approved
0.7244	Intermediate Similarity	NPD3892	Phase 2
0.7239	Intermediate Similarity	NPD7819	Suspended
0.7239	Intermediate Similarity	NPD5929	Approved
0.7234	Intermediate Similarity	NPD7340	Approved
0.7226	Intermediate Similarity	NPD1549	Phase 2
0.7226	Intermediate Similarity	NPD2424	Discontinued
0.7212	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4005	Discontinued
0.7186	Intermediate Similarity	NPD1247	Approved
0.7184	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8053	Approved
0.7184	Intermediate Similarity	NPD8054	Approved
0.7172	Intermediate Similarity	NPD422	Phase 1
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7157	Approved
0.7161	Intermediate Similarity	NPD3540	Phase 1
0.7153	Intermediate Similarity	NPD2684	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7135	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7132	Intermediate Similarity	NPD968	Approved
0.7125	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4750	Phase 3
0.7097	Intermediate Similarity	NPD2935	Discontinued
0.7097	Intermediate Similarity	NPD3539	Phase 1
0.7091	Intermediate Similarity	NPD2563	Approved
0.7091	Intermediate Similarity	NPD2560	Approved
0.7091	Intermediate Similarity	NPD5402	Approved
0.7089	Intermediate Similarity	NPD2677	Approved
0.7088	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD1357	Approved
0.708	Intermediate Similarity	NPD290	Approved
0.7075	Intermediate Similarity	NPD5327	Phase 3
0.7073	Intermediate Similarity	NPD3382	Approved
0.7073	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD3383	Approved
0.7073	Intermediate Similarity	NPD3384	Approved
0.7071	Intermediate Similarity	NPD7843	Approved
0.707	Intermediate Similarity	NPD4237	Approved
0.707	Intermediate Similarity	NPD4236	Phase 3
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7063	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3657	Discovery
0.7051	Intermediate Similarity	NPD6004	Phase 3
0.7051	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1375	Discontinued
0.7051	Intermediate Similarity	NPD6002	Phase 3
0.7051	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6005	Phase 3
0.7048	Intermediate Similarity	NPD7768	Phase 2
0.7047	Intermediate Similarity	NPD6584	Phase 3
0.7044	Intermediate Similarity	NPD7124	Phase 2
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7041	Intermediate Similarity	NPD6071	Discontinued
0.7034	Intermediate Similarity	NPD5125	Phase 3
0.7034	Intermediate Similarity	NPD5126	Approved
0.703	Intermediate Similarity	NPD8455	Phase 2
0.7025	Intermediate Similarity	NPD4535	Phase 3
0.7025	Intermediate Similarity	NPD3750	Approved
0.702	Intermediate Similarity	NPD7095	Approved
0.7013	Intermediate Similarity	NPD4097	Suspended
0.7012	Intermediate Similarity	NPD7411	Suspended

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