NPASS Compound

Structure

CID126284 OpenBabel06191715482D 22 26 0 0 1 0 0 0 0 0999 V2000 -2.5775 -4.1184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6110 0.4926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4073 0.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8025 0.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3951 -0.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1966 -3.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9894 -4.1118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6037 -2.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9109 0.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1919 -2.7303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7903 -0.8865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5865 -1.3604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6028 -1.3539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9851 -2.2724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9923 -1.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7926 -2.7334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5906 -2.2727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1904 -0.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7827 -3.6538 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -2.7373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2835 -0.7410 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 19 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 2 0 0 0 0 5 12 2 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 15 18 1 0 0 0 0 16 14 1 6 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.12
Volume:	298.651
LogP:	2.19
LogD:	2.516
LogS:	-3.087
# Rotatable Bonds:	0
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	3.474
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.694
MDCK Permeability:	3.352709245518781e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.857
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	86.83987426757812%
Volume Distribution (VD):	3.074
Pgp-substrate:	6.58202600479126%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.953
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.817

ADMET: Excretion

Clearance (CL):	16.038
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.129
AMES Toxicity:	0.908
Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.166
Carcinogencity:	0.629
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.839

Download Data

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

Natural Product: NPC126284

Natural Product ID:	NPC126284
*Common Name:**	Oliveroline
IUPAC Name:	n.a.
Synonyms:	Oliveroline
Standard InCHIKey:	NVMGTUCOAQKLLO-IRXDYDNUSA-N
Standard InCHI:	InChI=1S/C18H17NO3/c1-19-7-6-10-8-13-18(22-9-21-13)15-11-4-2-3-5-12(11)17(20)16(19)14(10)15/h2-5,8,16-17,20H,6-7,9H2,1H3/t16-,17-/m0/s1
SMILES:	CN1CCc2c3[C@H]1[C@@H](O)c1ccccc1c3c1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221034
PubChem CID:	12444634
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines [CHEMONTID:0003021] Hydroxy-7-aporphines

*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
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620236]
NPO17687	Duguetia odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315964]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25009	Cystoseira myrica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24939	Veronica officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13718	Poria tenuis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12599.1	Pinus leiophylla var. chihuahuana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24123	Ramalina scopulorum	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28729	Spirostachys africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17687	Duguetia odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24723	Ophiorrhiza bracteata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21816	Calea jamaicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25164	Polyalthia suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24593	Campanula pyramidalis	Species	Campanulaceae	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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	35.0	%	PMID[529966]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	45000.0	nM	PMID[529966]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20000.0	nM	PMID[529966]

☑ 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 NPC126284 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	331
0.1-0.2	1525
0.2-0.3	6885
0.3-0.4	11079
0.4-0.5	6103
0.5-0.6	12203
0.6-0.7	3699
0.7-0.8	576
0.8-0.85	187
0.85-0.9	72
0.9-0.95	30
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC248642
0.9818	High Similarity	NPC156576
0.9583	High Similarity	NPC214116
0.9521	High Similarity	NPC476575
0.9387	High Similarity	NPC298979
0.9383	High Similarity	NPC225774
0.9341	High Similarity	NPC320223
0.9341	High Similarity	NPC114364
0.9337	High Similarity	NPC128560
0.9337	High Similarity	NPC229166
0.9337	High Similarity	NPC199465
0.9325	High Similarity	NPC476432
0.9325	High Similarity	NPC219341
0.9325	High Similarity	NPC24264
0.9286	High Similarity	NPC267408
0.9268	High Similarity	NPC247389
0.9264	High Similarity	NPC302527
0.9264	High Similarity	NPC16805
0.9264	High Similarity	NPC167546
0.9249	High Similarity	NPC117717
0.9226	High Similarity	NPC148693
0.9226	High Similarity	NPC118633
0.9226	High Similarity	NPC294790
0.9198	High Similarity	NPC160298
0.9198	High Similarity	NPC232924
0.9198	High Similarity	NPC266753
0.9198	High Similarity	NPC306902
0.9198	High Similarity	NPC477559
0.9162	High Similarity	NPC2314
0.9152	High Similarity	NPC210918
0.9107	High Similarity	NPC477558
0.9075	High Similarity	NPC237579
0.9064	High Similarity	NPC116284
0.9064	High Similarity	NPC233718
0.9036	High Similarity	NPC150879
0.9012	High Similarity	NPC135772
0.9006	High Similarity	NPC476574
0.9006	High Similarity	NPC477561
0.9006	High Similarity	NPC312918
0.9006	High Similarity	NPC155442
0.8988	High Similarity	NPC149090
0.8988	High Similarity	NPC19520
0.8929	High Similarity	NPC6152
0.8929	High Similarity	NPC152212
0.8922	High Similarity	NPC12053
0.8922	High Similarity	NPC306555
0.8922	High Similarity	NPC158376
0.8922	High Similarity	NPC117188
0.8922	High Similarity	NPC145832
0.8922	High Similarity	NPC205421
0.8922	High Similarity	NPC81218
0.8922	High Similarity	NPC474931
0.8916	High Similarity	NPC78222
0.8916	High Similarity	NPC13504
0.8916	High Similarity	NPC253043
0.8916	High Similarity	NPC136508
0.8916	High Similarity	NPC477563
0.8916	High Similarity	NPC212794
0.8916	High Similarity	NPC196447
0.8916	High Similarity	NPC96603
0.8916	High Similarity	NPC306843
0.8869	High Similarity	NPC241055
0.8862	High Similarity	NPC86144
0.8862	High Similarity	NPC304659
0.8855	High Similarity	NPC1229
0.8855	High Similarity	NPC233650
0.8855	High Similarity	NPC324144
0.8848	High Similarity	NPC27410
0.8848	High Similarity	NPC166014
0.8844	High Similarity	NPC275132
0.8841	High Similarity	NPC476572
0.8834	High Similarity	NPC325871
0.8834	High Similarity	NPC99659
0.8807	High Similarity	NPC82763
0.8802	High Similarity	NPC134858
0.8802	High Similarity	NPC168409
0.88	High Similarity	NPC57036
0.8765	High Similarity	NPC81733
0.8765	High Similarity	NPC326316
0.8757	High Similarity	NPC475754
0.875	High Similarity	NPC476576
0.875	High Similarity	NPC186546
0.8743	High Similarity	NPC189470
0.8728	High Similarity	NPC220961
0.8721	High Similarity	NPC112575
0.8706	High Similarity	NPC168753
0.8706	High Similarity	NPC118274
0.8698	High Similarity	NPC210140
0.869	High Similarity	NPC169743
0.8678	High Similarity	NPC474506
0.8678	High Similarity	NPC32413
0.8671	High Similarity	NPC23219
0.8655	High Similarity	NPC225597
0.8655	High Similarity	NPC470739
0.8655	High Similarity	NPC477640
0.8655	High Similarity	NPC239775
0.8647	High Similarity	NPC82533
0.8647	High Similarity	NPC290759
0.8647	High Similarity	NPC266176
0.8647	High Similarity	NPC475686
0.8647	High Similarity	NPC158148
0.8647	High Similarity	NPC58766
0.8631	High Similarity	NPC320104
0.8621	High Similarity	NPC470879
0.8621	High Similarity	NPC258695
0.8605	High Similarity	NPC477020
0.8605	High Similarity	NPC66341
0.8605	High Similarity	NPC192135
0.8596	High Similarity	NPC69712
0.8596	High Similarity	NPC474475
0.8596	High Similarity	NPC477562
0.8596	High Similarity	NPC26240
0.8588	High Similarity	NPC190332
0.8588	High Similarity	NPC181653
0.858	High Similarity	NPC276944
0.858	High Similarity	NPC232514
0.858	High Similarity	NPC238530
0.8555	High Similarity	NPC187678
0.8539	High Similarity	NPC474904
0.8529	High Similarity	NPC35627
0.8529	High Similarity	NPC81247
0.8529	High Similarity	NPC476573
0.8514	High Similarity	NPC244554
0.8494	Intermediate Similarity	NPC244112
0.8494	Intermediate Similarity	NPC41178
0.8494	Intermediate Similarity	NPC216459
0.8494	Intermediate Similarity	NPC138487
0.8488	Intermediate Similarity	NPC311991
0.848	Intermediate Similarity	NPC100566
0.8466	Intermediate Similarity	NPC475959
0.8462	Intermediate Similarity	NPC60186
0.8452	Intermediate Similarity	NPC111485
0.8452	Intermediate Similarity	NPC477080
0.8443	Intermediate Similarity	NPC126519
0.8443	Intermediate Similarity	NPC146288
0.8443	Intermediate Similarity	NPC203784
0.8443	Intermediate Similarity	NPC170503
0.8421	Intermediate Similarity	NPC124657
0.8409	Intermediate Similarity	NPC474507
0.8402	Intermediate Similarity	NPC249274
0.8402	Intermediate Similarity	NPC97072
0.8402	Intermediate Similarity	NPC215829
0.84	Intermediate Similarity	NPC476577
0.84	Intermediate Similarity	NPC474470
0.84	Intermediate Similarity	NPC173416
0.84	Intermediate Similarity	NPC237044
0.84	Intermediate Similarity	NPC241704
0.84	Intermediate Similarity	NPC148709
0.8383	Intermediate Similarity	NPC76079
0.8373	Intermediate Similarity	NPC26601
0.8352	Intermediate Similarity	NPC474325
0.8343	Intermediate Similarity	NPC59028
0.8343	Intermediate Similarity	NPC304675
0.8343	Intermediate Similarity	NPC92191
0.8333	Intermediate Similarity	NPC312531
0.8333	Intermediate Similarity	NPC323443
0.8333	Intermediate Similarity	NPC180756
0.8333	Intermediate Similarity	NPC234392
0.8333	Intermediate Similarity	NPC31311
0.8306	Intermediate Similarity	NPC162653
0.8305	Intermediate Similarity	NPC474745
0.8305	Intermediate Similarity	NPC32154
0.8303	Intermediate Similarity	NPC219162
0.8303	Intermediate Similarity	NPC211296
0.8294	Intermediate Similarity	NPC4304
0.8294	Intermediate Similarity	NPC205167
0.8293	Intermediate Similarity	NPC476151
0.8282	Intermediate Similarity	NPC185838
0.8276	Intermediate Similarity	NPC329911
0.8266	Intermediate Similarity	NPC204947
0.8263	Intermediate Similarity	NPC210148
0.8263	Intermediate Similarity	NPC233029
0.8258	Intermediate Similarity	NPC179704
0.8256	Intermediate Similarity	NPC247972
0.8249	Intermediate Similarity	NPC15919
0.8225	Intermediate Similarity	NPC186063
0.8222	Intermediate Similarity	NPC9867
0.8218	Intermediate Similarity	NPC160570
0.8212	Intermediate Similarity	NPC249405
0.8208	Intermediate Similarity	NPC476002
0.8202	Intermediate Similarity	NPC99179
0.8197	Intermediate Similarity	NPC78284
0.8193	Intermediate Similarity	NPC103379
0.8193	Intermediate Similarity	NPC477565
0.8192	Intermediate Similarity	NPC287588
0.8182	Intermediate Similarity	NPC253883
0.8182	Intermediate Similarity	NPC90844
0.8182	Intermediate Similarity	NPC95075
0.8182	Intermediate Similarity	NPC321505
0.8182	Intermediate Similarity	NPC179825
0.8182	Intermediate Similarity	NPC191376
0.8171	Intermediate Similarity	NPC75958
0.8171	Intermediate Similarity	NPC145304
0.8167	Intermediate Similarity	NPC474746
0.8167	Intermediate Similarity	NPC475981
0.8166	Intermediate Similarity	NPC93593
0.8166	Intermediate Similarity	NPC204828
0.8166	Intermediate Similarity	NPC5238
0.8166	Intermediate Similarity	NPC249797
0.8166	Intermediate Similarity	NPC78733

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 NPC126284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	714
0.2-0.3	1085
0.3-0.4	2139
0.4-0.5	2590
0.5-0.6	1650
0.6-0.7	623
0.7-0.8	130
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8639	High Similarity	NPD3051	Approved
0.8588	High Similarity	NPD2969	Approved
0.8588	High Similarity	NPD2970	Approved
0.843	Intermediate Similarity	NPD2489	Approved
0.843	Intermediate Similarity	NPD27	Approved
0.838	Intermediate Similarity	NPD7906	Approved
0.8362	Intermediate Similarity	NPD4578	Approved
0.8362	Intermediate Similarity	NPD4577	Approved
0.8333	Intermediate Similarity	NPD5241	Discontinued
0.8333	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD4663	Approved
0.8121	Intermediate Similarity	NPD2420	Approved
0.8121	Intermediate Similarity	NPD2421	Approved
0.8114	Intermediate Similarity	NPD4481	Phase 3
0.8072	Intermediate Similarity	NPD4584	Approved
0.8061	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6071	Discontinued
0.7989	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD2563	Approved
0.7965	Intermediate Similarity	NPD2560	Approved
0.7956	Intermediate Similarity	NPD7310	Approved
0.7956	Intermediate Similarity	NPD7313	Approved
0.7956	Intermediate Similarity	NPD7312	Approved
0.7956	Intermediate Similarity	NPD7311	Approved
0.7912	Intermediate Similarity	NPD7309	Approved
0.7907	Intermediate Similarity	NPD2977	Approved
0.7907	Intermediate Similarity	NPD2978	Approved
0.7892	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2973	Approved
0.7872	Intermediate Similarity	NPD2975	Approved
0.7872	Intermediate Similarity	NPD2974	Approved
0.7801	Intermediate Similarity	NPD2494	Approved
0.7801	Intermediate Similarity	NPD3450	Approved
0.7801	Intermediate Similarity	NPD3452	Approved
0.7801	Intermediate Similarity	NPD2493	Approved
0.7796	Intermediate Similarity	NPD2490	Approved
0.7796	Intermediate Similarity	NPD2488	Approved
0.7791	Intermediate Similarity	NPD4772	Phase 2
0.7791	Intermediate Similarity	NPD4773	Phase 2
0.7771	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7831	Phase 2
0.7771	Intermediate Similarity	NPD7833	Phase 2
0.776	Intermediate Similarity	NPD2971	Approved
0.776	Intermediate Similarity	NPD2968	Approved
0.7749	Intermediate Similarity	NPD4580	Approved
0.7737	Intermediate Similarity	NPD4420	Approved
0.7717	Intermediate Similarity	NPD8054	Approved
0.7717	Intermediate Similarity	NPD8053	Approved
0.7709	Intermediate Similarity	NPD2898	Approved
0.768	Intermediate Similarity	NPD4582	Approved
0.768	Intermediate Similarity	NPD4583	Approved
0.768	Intermediate Similarity	NPD8156	Discontinued
0.7665	Intermediate Similarity	NPD4237	Approved
0.7665	Intermediate Similarity	NPD4236	Phase 3
0.7632	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD4004	Approved
0.7629	Intermediate Similarity	NPD4002	Approved
0.7624	Intermediate Similarity	NPD8251	Approved
0.7624	Intermediate Similarity	NPD8099	Discontinued
0.7624	Intermediate Similarity	NPD8252	Approved
0.7614	Intermediate Similarity	NPD6788	Approved
0.7614	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD5005	Approved
0.7577	Intermediate Similarity	NPD5006	Approved
0.7572	Intermediate Similarity	NPD4017	Approved
0.7544	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1753	Discontinued
0.75	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7047	Phase 3
0.7472	Intermediate Similarity	NPD5604	Discontinued
0.7457	Intermediate Similarity	NPD4727	Phase 1
0.7456	Intermediate Similarity	NPD5177	Phase 3
0.7456	Intermediate Similarity	NPD3060	Approved
0.7448	Intermediate Similarity	NPD5582	Discontinued
0.7443	Intermediate Similarity	NPD7298	Approved
0.743	Intermediate Similarity	NPD7400	Phase 3
0.7427	Intermediate Similarity	NPD6997	Phase 2
0.7427	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3845	Phase 1
0.7425	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4010	Discontinued
0.7398	Intermediate Similarity	NPD3057	Approved
0.7394	Intermediate Similarity	NPD3109	Approved
0.7394	Intermediate Similarity	NPD3110	Approved
0.7391	Intermediate Similarity	NPD6042	Phase 2
0.7391	Intermediate Similarity	NPD42	Phase 2
0.7356	Intermediate Similarity	NPD3640	Phase 3
0.7356	Intermediate Similarity	NPD6030	Approved
0.7356	Intermediate Similarity	NPD5976	Discontinued
0.7356	Intermediate Similarity	NPD3641	Approved
0.7356	Intermediate Similarity	NPD3639	Approved
0.7356	Intermediate Similarity	NPD6031	Approved
0.7337	Intermediate Similarity	NPD4721	Approved
0.7337	Intermediate Similarity	NPD4725	Approved
0.7337	Intermediate Similarity	NPD4726	Approved
0.7333	Intermediate Similarity	NPD5709	Phase 3
0.7327	Intermediate Similarity	NPD7827	Phase 1
0.7312	Intermediate Similarity	NPD6297	Approved
0.731	Intermediate Similarity	NPD3533	Approved
0.731	Intermediate Similarity	NPD2972	Approved
0.7303	Intermediate Similarity	NPD5773	Approved
0.7303	Intermediate Similarity	NPD5772	Approved
0.7293	Intermediate Similarity	NPD4666	Phase 3
0.7287	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5160	Discontinued
0.7253	Intermediate Similarity	NPD6107	Approved
0.7249	Intermediate Similarity	NPD6853	Approved
0.7249	Intermediate Similarity	NPD6851	Approved
0.7249	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4040	Phase 1
0.7234	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6666	Approved
0.7225	Intermediate Similarity	NPD6667	Approved
0.7222	Intermediate Similarity	NPD2491	Approved
0.7222	Intermediate Similarity	NPD3448	Approved
0.7212	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5754	Discontinued
0.72	Intermediate Similarity	NPD6090	Discontinued
0.7196	Intermediate Similarity	NPD7280	Phase 3
0.7196	Intermediate Similarity	NPD7281	Phase 3
0.7193	Intermediate Similarity	NPD7037	Approved
0.7192	Intermediate Similarity	NPD5676	Approved
0.7189	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4055	Discovery
0.7175	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4005	Discontinued
0.7169	Intermediate Similarity	NPD5718	Phase 2
0.7157	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4123	Phase 3
0.7126	Intermediate Similarity	NPD4475	Approved
0.7126	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4474	Approved
0.7121	Intermediate Similarity	NPD4107	Approved
0.7108	Intermediate Similarity	NPD5155	Approved
0.7108	Intermediate Similarity	NPD5156	Approved
0.7101	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5938	Phase 3
0.7083	Intermediate Similarity	NPD2238	Phase 2
0.7079	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7262	Phase 1
0.7069	Intermediate Similarity	NPD3692	Discontinued
0.7065	Intermediate Similarity	NPD7802	Discontinued
0.7062	Intermediate Similarity	NPD1914	Approved
0.7062	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6674	Discontinued
0.7052	Intermediate Similarity	NPD4162	Approved
0.7048	Intermediate Similarity	NPD2605	Approved
0.7048	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2606	Approved
0.7048	Intermediate Similarity	NPD3595	Approved
0.7048	Intermediate Similarity	NPD7907	Approved
0.7048	Intermediate Similarity	NPD3594	Approved
0.7045	Intermediate Similarity	NPD1424	Approved
0.7035	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4665	Approved
0.7033	Intermediate Similarity	NPD4111	Phase 1
0.7027	Intermediate Similarity	NPD4166	Phase 2
0.7022	Intermediate Similarity	NPD4210	Discontinued
0.7018	Intermediate Similarity	NPD4108	Discontinued
0.7011	Intermediate Similarity	NPD6331	Phase 2
0.7011	Intermediate Similarity	NPD6037	Discontinued
0.701	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6072	Discontinued
0.7	Intermediate Similarity	NPD4482	Phase 3
0.6989	Remote Similarity	NPD7213	Phase 3
0.6989	Remote Similarity	NPD7212	Phase 2
0.6989	Remote Similarity	NPD6688	Approved
0.6989	Remote Similarity	NPD6687	Approved
0.6989	Remote Similarity	NPD3124	Discontinued
0.6988	Remote Similarity	NPD3637	Approved
0.6988	Remote Similarity	NPD3635	Approved
0.6988	Remote Similarity	NPD3636	Approved
0.6974	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2677	Approved
0.697	Remote Similarity	NPD4103	Phase 2
0.697	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD37	Approved
0.6961	Remote Similarity	NPD4859	Phase 1
0.6952	Remote Similarity	NPD3763	Approved
0.6951	Remote Similarity	NPD4659	Approved
0.6949	Remote Similarity	NPD7447	Phase 1
0.6949	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7007	Discovery
0.6944	Remote Similarity	NPD4678	Approved
0.6944	Remote Similarity	NPD4675	Approved
0.6943	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1375	Discontinued
0.6936	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7030	Discontinued
0.6931	Remote Similarity	NPD5312	Approved
0.6931	Remote Similarity	NPD5095	Phase 3
0.6931	Remote Similarity	NPD5096	Phase 3
0.6931	Remote Similarity	NPD5313	Approved

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