NPASS Compound

Structure

CID248642 OpenBabel06191716052D 24 28 0 0 1 0 0 0 0 0999 V2000 -2.5935 -4.1440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2484 1.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6272 0.4957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8137 0.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1978 -3.6776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9956 -4.1373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6074 -2.2828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4162 -0.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9166 0.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1931 -2.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4285 0.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8014 -0.8921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6026 -1.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6066 -1.3623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9912 -2.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9985 -1.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8037 -2.7504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6067 -2.2868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1916 -0.9015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7938 -3.6765 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4064 -2.7543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2361 0.4711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2915 -0.7456 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 20 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 20 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 15 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 16 19 1 0 0 0 0 17 15 1 6 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 1 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.342
LogD:	2.577
LogS:	-3.171
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.873
Synthetic Accessibility Score:	3.524
Fsp3:	0.368
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:	-4.739
MDCK Permeability:	4.027055547339842e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.546
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	85.3341293334961%
Volume Distribution (VD):	2.865
Pgp-substrate:	6.769080638885498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.434
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.884

ADMET: Excretion

Clearance (CL):	15.438
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.402
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.302
AMES Toxicity:	0.846
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.223
Carcinogencity:	0.475
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC248642

Natural Product ID:	NPC248642
*Common Name:**	Oliveridine
IUPAC Name:	n.a.
Synonyms:	Oliveridine
Standard InCHIKey:	HKTOYUUCGONYEC-ROUUACIJSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-20-6-5-10-7-14-19(24-9-23-14)16-12-4-3-11(22-2)8-13(12)18(21)17(20)15(10)16/h3-4,7-8,17-18,21H,5-6,9H2,1-2H3/t17-,18-/m0/s1
SMILES:	COc1ccc2c(c1)[C@H](O)[C@@H]1c3c2c2OCOc2cc3CCN1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506088
PubChem CID:	13891891
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]
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]
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]
NPO9266	Stephania delavayi	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9266	Stephania delavayi	Species	Menispermaceae	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]
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[TCM_Taiwan]
NPO9266	Stephania delavayi	Species	Menispermaceae	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]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9266	Stephania delavayi	Species	Menispermaceae	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]
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]
NPO21816	Calea jamaicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	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]
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]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	7000.0	nM	PMID[489813]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MTC	=	5.0	uM	PMID[489813]

☑ 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 NPC248642 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	329
0.1-0.2	1503
0.2-0.3	6254
0.3-0.4	11548
0.4-0.5	5887
0.5-0.6	12166
0.6-0.7	4065
0.7-0.8	642
0.8-0.85	183
0.85-0.9	82
0.9-0.95	30
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC156576
0.9878	High Similarity	NPC126284
0.9586	High Similarity	NPC214116
0.9461	High Similarity	NPC114364
0.9461	High Similarity	NPC320223
0.9408	High Similarity	NPC476575
0.939	High Similarity	NPC247389
0.9341	High Similarity	NPC128560
0.9341	High Similarity	NPC199465
0.9341	High Similarity	NPC229166
0.9329	High Similarity	NPC476432
0.9329	High Similarity	NPC24264
0.9329	High Similarity	NPC219341
0.9281	High Similarity	NPC2314
0.9273	High Similarity	NPC298979
0.9268	High Similarity	NPC302527
0.9268	High Similarity	NPC16805
0.9268	High Similarity	NPC225774
0.9268	High Similarity	NPC167546
0.9253	High Similarity	NPC117717
0.9231	High Similarity	NPC118633
0.9231	High Similarity	NPC294790
0.9231	High Similarity	NPC148693
0.9176	High Similarity	NPC267408
0.9157	High Similarity	NPC210918
0.9128	High Similarity	NPC135772
0.9085	High Similarity	NPC306902
0.9085	High Similarity	NPC160298
0.9085	High Similarity	NPC232924
0.9085	High Similarity	NPC477559
0.9085	High Similarity	NPC266753
0.908	High Similarity	NPC237579
0.907	High Similarity	NPC233718
0.907	High Similarity	NPC116284
0.9042	High Similarity	NPC145832
0.9042	High Similarity	NPC306555
0.9042	High Similarity	NPC474931
0.9042	High Similarity	NPC12053
0.9042	High Similarity	NPC81218
0.9042	High Similarity	NPC158376
0.9042	High Similarity	NPC150879
0.9042	High Similarity	NPC117188
0.9042	High Similarity	NPC205421
0.9012	High Similarity	NPC477561
0.9012	High Similarity	NPC155442
0.9012	High Similarity	NPC312918
0.9012	High Similarity	NPC476574
0.9	High Similarity	NPC477558
0.8994	High Similarity	NPC149090
0.8994	High Similarity	NPC19520
0.8963	High Similarity	NPC476572
0.8935	High Similarity	NPC6152
0.8922	High Similarity	NPC136508
0.8922	High Similarity	NPC477563
0.8922	High Similarity	NPC96603
0.8922	High Similarity	NPC196447
0.8922	High Similarity	NPC212794
0.8922	High Similarity	NPC306843
0.8922	High Similarity	NPC13504
0.8922	High Similarity	NPC78222
0.8922	High Similarity	NPC253043
0.8914	High Similarity	NPC57036
0.887	High Similarity	NPC475754
0.8862	High Similarity	NPC1229
0.8862	High Similarity	NPC233650
0.8862	High Similarity	NPC324144
0.8851	High Similarity	NPC275132
0.8841	High Similarity	NPC99659
0.8841	High Similarity	NPC325871
0.8824	High Similarity	NPC152212
0.8814	High Similarity	NPC82763
0.881	High Similarity	NPC134858
0.8793	High Similarity	NPC474506
0.8793	High Similarity	NPC32413
0.8772	High Similarity	NPC225597
0.8772	High Similarity	NPC477640
0.8772	High Similarity	NPC470739
0.8765	High Similarity	NPC241055
0.8757	High Similarity	NPC304659
0.8757	High Similarity	NPC476576
0.8757	High Similarity	NPC186546
0.8757	High Similarity	NPC86144
0.8743	High Similarity	NPC166014
0.8743	High Similarity	NPC27410
0.8736	High Similarity	NPC470879
0.8736	High Similarity	NPC220961
0.8736	High Similarity	NPC258695
0.8721	High Similarity	NPC192135
0.8721	High Similarity	NPC66341
0.8721	High Similarity	NPC477020
0.8713	High Similarity	NPC474475
0.8706	High Similarity	NPC210140
0.8698	High Similarity	NPC169743
0.8698	High Similarity	NPC168409
0.8678	High Similarity	NPC23219
0.8663	High Similarity	NPC239775
0.8659	High Similarity	NPC326316
0.8659	High Similarity	NPC81733
0.8655	High Similarity	NPC266176
0.8655	High Similarity	NPC475686
0.8655	High Similarity	NPC158148
0.8655	High Similarity	NPC58766
0.8655	High Similarity	NPC290759
0.8655	High Similarity	NPC82533
0.8639	High Similarity	NPC189470
0.8621	High Similarity	NPC112575
0.8605	High Similarity	NPC477562
0.8605	High Similarity	NPC168753
0.8605	High Similarity	NPC118274
0.8605	High Similarity	NPC69712
0.8605	High Similarity	NPC26240
0.8596	High Similarity	NPC190332
0.8596	High Similarity	NPC181653
0.8588	High Similarity	NPC232514
0.8588	High Similarity	NPC238530
0.8588	High Similarity	NPC276944
0.8563	High Similarity	NPC187678
0.8529	High Similarity	NPC320104
0.8523	High Similarity	NPC244554
0.8503	High Similarity	NPC138487
0.8503	High Similarity	NPC216459
0.8503	High Similarity	NPC244112
0.8503	High Similarity	NPC41178
0.8497	Intermediate Similarity	NPC311991
0.8488	Intermediate Similarity	NPC100566
0.8476	Intermediate Similarity	NPC475959
0.8471	Intermediate Similarity	NPC60186
0.8462	Intermediate Similarity	NPC59028
0.8462	Intermediate Similarity	NPC92191
0.8462	Intermediate Similarity	NPC111485
0.8452	Intermediate Similarity	NPC146288
0.8444	Intermediate Similarity	NPC474904
0.843	Intermediate Similarity	NPC476573
0.843	Intermediate Similarity	NPC35627
0.843	Intermediate Similarity	NPC81247
0.8418	Intermediate Similarity	NPC474507
0.8415	Intermediate Similarity	NPC162653
0.8412	Intermediate Similarity	NPC4304
0.8409	Intermediate Similarity	NPC241704
0.8409	Intermediate Similarity	NPC237044
0.8409	Intermediate Similarity	NPC474470
0.8362	Intermediate Similarity	NPC474325
0.8353	Intermediate Similarity	NPC477080
0.8352	Intermediate Similarity	NPC304675
0.8343	Intermediate Similarity	NPC31311
0.8343	Intermediate Similarity	NPC126519
0.8343	Intermediate Similarity	NPC312531
0.8343	Intermediate Similarity	NPC170503
0.8343	Intermediate Similarity	NPC234392
0.8343	Intermediate Similarity	NPC203784
0.8333	Intermediate Similarity	NPC9867
0.8324	Intermediate Similarity	NPC476002
0.8324	Intermediate Similarity	NPC124657
0.8315	Intermediate Similarity	NPC474745
0.8315	Intermediate Similarity	NPC32154
0.8315	Intermediate Similarity	NPC99179
0.8313	Intermediate Similarity	NPC211296
0.8306	Intermediate Similarity	NPC78284
0.8305	Intermediate Similarity	NPC173416
0.8305	Intermediate Similarity	NPC148709
0.8305	Intermediate Similarity	NPC476577
0.8304	Intermediate Similarity	NPC205167
0.8304	Intermediate Similarity	NPC249274
0.8304	Intermediate Similarity	NPC215829
0.8304	Intermediate Similarity	NPC97072
0.8286	Intermediate Similarity	NPC329911
0.8284	Intermediate Similarity	NPC76079
0.8276	Intermediate Similarity	NPC252960
0.8276	Intermediate Similarity	NPC204947
0.8274	Intermediate Similarity	NPC26601
0.8274	Intermediate Similarity	NPC233029
0.8274	Intermediate Similarity	NPC210148
0.8268	Intermediate Similarity	NPC179704
0.8258	Intermediate Similarity	NPC15919
0.8249	Intermediate Similarity	NPC49353
0.8235	Intermediate Similarity	NPC186063
0.8235	Intermediate Similarity	NPC323443
0.8235	Intermediate Similarity	NPC180756
0.8229	Intermediate Similarity	NPC160570
0.8208	Intermediate Similarity	NPC218614
0.8204	Intermediate Similarity	NPC219162
0.8202	Intermediate Similarity	NPC287588
0.8193	Intermediate Similarity	NPC476151
0.8182	Intermediate Similarity	NPC75958
0.8182	Intermediate Similarity	NPC185838
0.8177	Intermediate Similarity	NPC475981
0.8177	Intermediate Similarity	NPC474746
0.8176	Intermediate Similarity	NPC295691
0.8176	Intermediate Similarity	NPC193949
0.8176	Intermediate Similarity	NPC127674
0.8176	Intermediate Similarity	NPC39701
0.8176	Intermediate Similarity	NPC54379
0.8176	Intermediate Similarity	NPC189266
0.8176	Intermediate Similarity	NPC207757
0.8176	Intermediate Similarity	NPC184026
0.8176	Intermediate Similarity	NPC2413
0.8176	Intermediate Similarity	NPC204828
0.8176	Intermediate Similarity	NPC276588
0.8176	Intermediate Similarity	NPC5238
0.8176	Intermediate Similarity	NPC249797

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 NPC248642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	711
0.2-0.3	1054
0.3-0.4	2187
0.4-0.5	2583
0.5-0.6	1640
0.6-0.7	634
0.7-0.8	132
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD3051	Approved
0.8492	Intermediate Similarity	NPD7906	Approved
0.8488	Intermediate Similarity	NPD2969	Approved
0.8488	Intermediate Similarity	NPD2970	Approved
0.8436	Intermediate Similarity	NPD4663	Approved
0.8371	Intermediate Similarity	NPD4577	Approved
0.8371	Intermediate Similarity	NPD4578	Approved
0.8343	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2489	Approved
0.8333	Intermediate Similarity	NPD27	Approved
0.8232	Intermediate Similarity	NPD5241	Discontinued
0.8125	Intermediate Similarity	NPD4481	Phase 3
0.8084	Intermediate Similarity	NPD4584	Approved
0.8066	Intermediate Similarity	NPD7313	Approved
0.8066	Intermediate Similarity	NPD7312	Approved
0.8066	Intermediate Similarity	NPD7310	Approved
0.8066	Intermediate Similarity	NPD7311	Approved
0.8049	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD2420	Approved
0.8024	Intermediate Similarity	NPD2421	Approved
0.8023	Intermediate Similarity	NPD2978	Approved
0.8023	Intermediate Similarity	NPD2977	Approved
0.8022	Intermediate Similarity	NPD7309	Approved
0.7979	Intermediate Similarity	NPD2975	Approved
0.7979	Intermediate Similarity	NPD2974	Approved
0.7979	Intermediate Similarity	NPD2973	Approved
0.7964	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6071	Discontinued
0.7906	Intermediate Similarity	NPD3452	Approved
0.7906	Intermediate Similarity	NPD3450	Approved
0.7906	Intermediate Similarity	NPD2494	Approved
0.7906	Intermediate Similarity	NPD2493	Approved
0.7898	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD2563	Approved
0.7874	Intermediate Similarity	NPD2560	Approved
0.7853	Intermediate Similarity	NPD4580	Approved
0.7842	Intermediate Similarity	NPD4420	Approved
0.7798	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4583	Approved
0.7784	Intermediate Similarity	NPD4582	Approved
0.7732	Intermediate Similarity	NPD4004	Approved
0.7732	Intermediate Similarity	NPD4002	Approved
0.773	Intermediate Similarity	NPD8054	Approved
0.773	Intermediate Similarity	NPD8053	Approved
0.7713	Intermediate Similarity	NPD2488	Approved
0.7713	Intermediate Similarity	NPD2490	Approved
0.7701	Intermediate Similarity	NPD4772	Phase 2
0.7701	Intermediate Similarity	NPD4773	Phase 2
0.7692	Intermediate Similarity	NPD8156	Discontinued
0.7684	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7831	Phase 2
0.7684	Intermediate Similarity	NPD7833	Phase 2
0.768	Intermediate Similarity	NPD5006	Approved
0.768	Intermediate Similarity	NPD5005	Approved
0.7679	Intermediate Similarity	NPD4236	Phase 3
0.7679	Intermediate Similarity	NPD4237	Approved
0.7676	Intermediate Similarity	NPD2968	Approved
0.7676	Intermediate Similarity	NPD2971	Approved
0.7644	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8251	Approved
0.7637	Intermediate Similarity	NPD8099	Discontinued
0.7637	Intermediate Similarity	NPD8252	Approved
0.7627	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2898	Approved
0.7606	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7047	Phase 3
0.7552	Intermediate Similarity	NPD5582	Discontinued
0.7545	Intermediate Similarity	NPD1753	Discontinued
0.7528	Intermediate Similarity	NPD6788	Approved
0.7524	Intermediate Similarity	NPD6997	Phase 2
0.75	Intermediate Similarity	NPD42	Phase 2
0.75	Intermediate Similarity	NPD6042	Phase 2
0.7486	Intermediate Similarity	NPD5604	Discontinued
0.7486	Intermediate Similarity	NPD4017	Approved
0.7471	Intermediate Similarity	NPD5177	Phase 3
0.7471	Intermediate Similarity	NPD4727	Phase 1
0.7471	Intermediate Similarity	NPD3060	Approved
0.7458	Intermediate Similarity	NPD7298	Approved
0.7457	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4010	Discontinued
0.7416	Intermediate Similarity	NPD5773	Approved
0.7416	Intermediate Similarity	NPD5772	Approved
0.7384	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6030	Approved
0.7371	Intermediate Similarity	NPD6031	Approved
0.7348	Intermediate Similarity	NPD5709	Phase 3
0.7348	Intermediate Similarity	NPD7400	Phase 3
0.7341	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3845	Phase 1
0.734	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7827	Phase 1
0.7337	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6297	Approved
0.7323	Intermediate Similarity	NPD3057	Approved
0.7314	Intermediate Similarity	NPD6090	Discontinued
0.7308	Intermediate Similarity	NPD4666	Phase 3
0.7305	Intermediate Similarity	NPD3110	Approved
0.7305	Intermediate Similarity	NPD3109	Approved
0.7302	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3641	Approved
0.7273	Intermediate Similarity	NPD3639	Approved
0.7273	Intermediate Similarity	NPD5976	Discontinued
0.7273	Intermediate Similarity	NPD3640	Phase 3
0.7268	Intermediate Similarity	NPD6107	Approved
0.7263	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6853	Approved
0.7263	Intermediate Similarity	NPD6851	Approved
0.7259	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4123	Phase 3
0.7251	Intermediate Similarity	NPD4726	Approved
0.7251	Intermediate Similarity	NPD4725	Approved
0.7251	Intermediate Similarity	NPD4721	Approved
0.7236	Intermediate Similarity	NPD3533	Approved
0.7236	Intermediate Similarity	NPD2972	Approved
0.7211	Intermediate Similarity	NPD7280	Phase 3
0.7211	Intermediate Similarity	NPD7281	Phase 3
0.7206	Intermediate Similarity	NPD5676	Approved
0.7198	Intermediate Similarity	NPD4055	Discovery
0.7191	Intermediate Similarity	NPD4005	Discontinued
0.7184	Intermediate Similarity	NPD5160	Discontinued
0.7168	Intermediate Similarity	NPD6674	Discontinued
0.7167	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4040	Phase 1
0.7156	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2491	Approved
0.715	Intermediate Similarity	NPD3448	Approved
0.7143	Intermediate Similarity	NPD7907	Approved
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7136	Intermediate Similarity	NPD4107	Approved
0.7129	Intermediate Similarity	NPD4111	Phase 1
0.7129	Intermediate Similarity	NPD4665	Approved
0.7126	Intermediate Similarity	NPD5754	Discontinued
0.7126	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7037	Approved
0.7101	Intermediate Similarity	NPD2238	Phase 2
0.7095	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3692	Discontinued
0.7086	Intermediate Similarity	NPD2677	Approved
0.7083	Intermediate Similarity	NPD5718	Phase 2
0.7081	Intermediate Similarity	NPD7802	Discontinued
0.7077	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD37	Approved
0.7069	Intermediate Similarity	NPD4162	Approved
0.7056	Intermediate Similarity	NPD4675	Approved
0.7056	Intermediate Similarity	NPD4678	Approved
0.7053	Intermediate Similarity	NPD7007	Discovery
0.7052	Intermediate Similarity	NPD1375	Discontinued
0.7052	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4475	Approved
0.7041	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4474	Approved
0.7039	Intermediate Similarity	NPD3686	Approved
0.7039	Intermediate Similarity	NPD3687	Approved
0.7039	Intermediate Similarity	NPD4210	Discontinued
0.7035	Intermediate Similarity	NPD4108	Discontinued
0.7027	Intermediate Similarity	NPD5677	Discontinued
0.7026	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5155	Approved
0.7024	Intermediate Similarity	NPD5156	Approved
0.7021	Intermediate Similarity	NPD5938	Phase 3
0.7018	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6072	Discontinued
0.7016	Intermediate Similarity	NPD7038	Approved
0.7016	Intermediate Similarity	NPD7039	Approved
0.7015	Intermediate Similarity	NPD4482	Phase 3
0.7006	Intermediate Similarity	NPD7213	Phase 3
0.7006	Intermediate Similarity	NPD7212	Phase 2
0.7005	Intermediate Similarity	NPD7262	Phase 1
0.7005	Intermediate Similarity	NPD6687	Approved
0.7005	Intermediate Similarity	NPD6688	Approved
0.7	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1914	Approved
0.6979	Remote Similarity	NPD7549	Discontinued
0.6976	Remote Similarity	NPD4859	Phase 1
0.6967	Remote Similarity	NPD3763	Approved
0.6966	Remote Similarity	NPD7447	Phase 1
0.6966	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1424	Approved
0.6964	Remote Similarity	NPD2605	Approved
0.6964	Remote Similarity	NPD3594	Approved
0.6964	Remote Similarity	NPD3595	Approved
0.6964	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2606	Approved
0.6959	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD4967	Phase 2
0.6957	Remote Similarity	NPD4965	Approved
0.6955	Remote Similarity	NPD7048	Phase 3
0.6954	Remote Similarity	NPD7296	Approved
0.6952	Remote Similarity	NPD4166	Phase 2
0.6947	Remote Similarity	NPD5312	Approved
0.6947	Remote Similarity	NPD5313	Approved
0.6947	Remote Similarity	NPD5096	Phase 3
0.6947	Remote Similarity	NPD8153	Approved
0.6947	Remote Similarity	NPD8152	Approved
0.6947	Remote Similarity	NPD5095	Phase 3

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