NPASS Compound

Structure

CID273959 OpenBabel06191716082D 30 34 0 0 1 0 0 0 0 0999 V2000 -3.9049 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 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 10 2 0 0 0 0 2 10 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 8 18 1 0 0 0 0 9 28 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 10 1 1 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 18 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 9 1 6 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 11 1 6 0 0 0 20 22 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 22 25 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.14
Volume:	404.022
LogP:	4.569
LogD:	3.405
LogS:	-5.536
# Rotatable Bonds:	3
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	3.999
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.824
MDCK Permeability:	2.3553659048047848e-05
Pgp-inhibitor:	0.429
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	95.91947174072266%
Volume Distribution (VD):	0.723
Pgp-substrate:	4.479727268218994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.823
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.638
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.514

ADMET: Excretion

Clearance (CL):	8.399
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.477
Drug-inuced Liver Injury (DILI):	0.884
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.613
Carcinogencity:	0.152
Eye Corrosion:	0.003
Eye Irritation:	0.352
Respiratory Toxicity:	0.756

Download Data

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

Natural Product: NPC273959

Natural Product ID:	NPC273959
*Common Name:**	Sumatrol
IUPAC Name:	n.a.
Synonyms:	Sumatrol
Standard InCHIKey:	ZPEHYKMRUBEPSQ-XMCHAPAWSA-N
Standard InCHI:	InChI=1S/C23H22O7/c1-10(2)14-6-12-16(29-14)7-13(24)21-22(25)20-11-5-17(26-3)18(27-4)8-15(11)28-9-19(20)30-23(12)21/h5,7-8,14,19-20,24H,1,6,9H2,2-4H3/t14-,19-,20+/m1/s1
SMILES:	COc1cc2OC[C@@H]3[C@H](c2cc1OC)C(=O)c1c(O3)c2C[C@@H](Oc2cc1O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518045
PubChem CID:	442824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO8274	Geijera parviflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23848189]
NPO6485	Spiraea japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24684844]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[26434122]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6485	Spiraea japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25400	Derris malaccensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25400	Derris malaccensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1007	Crotalaria paniculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6485	Spiraea japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25400	Derris malaccensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8274	Geijera parviflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11864	Aflatunia ulmifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25400	Derris malaccensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25815	Asparagopsis sandfordiana	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25367	Macaranga vedeliana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25978	Ochrosia sandwicensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6485	Spiraea japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10600	Dysoxylum spectabile	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1007	Crotalaria paniculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15101	Tricholoma panaeolum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO323	Trachelanthus hissaricus	Species	Boraginaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	>	23.0	uM	PMID[549149]
NPT27	Others	Unspecified		IC50	>	47000.0	nM	PMID[549149]
NPT2	Others	Unspecified		Inhibition	=	49.9	%	PMID[549149]

☑ 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 NPC273959 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	418
0.1-0.2	1563
0.2-0.3	3643
0.3-0.4	8960
0.4-0.5	9562
0.5-0.6	3392
0.6-0.7	4861
0.7-0.8	5635
0.8-0.85	2740
0.85-0.9	1622
0.9-0.95	287
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC128293
0.962	High Similarity	NPC120593
0.962	High Similarity	NPC173292
0.9557	High Similarity	NPC326520
0.9551	High Similarity	NPC298093
0.95	High Similarity	NPC152477
0.9497	High Similarity	NPC170245
0.949	High Similarity	NPC474186
0.9437	High Similarity	NPC117854
0.9437	High Similarity	NPC6588
0.9437	High Similarity	NPC477154
0.9434	High Similarity	NPC25361
0.943	High Similarity	NPC81679
0.9427	High Similarity	NPC475886
0.9427	High Similarity	NPC474287
0.9423	High Similarity	NPC223787
0.9423	High Similarity	NPC165977
0.9423	High Similarity	NPC217677
0.9423	High Similarity	NPC181960
0.9423	High Similarity	NPC469584
0.9419	High Similarity	NPC472909
0.9419	High Similarity	NPC37392
0.9383	High Similarity	NPC121333
0.9383	High Similarity	NPC223375
0.9383	High Similarity	NPC475825
0.9379	High Similarity	NPC242395
0.9371	High Similarity	NPC329669
0.9371	High Similarity	NPC152659
0.9371	High Similarity	NPC472278
0.9371	High Similarity	NPC236521
0.9371	High Similarity	NPC18100
0.9371	High Similarity	NPC473313
0.9371	High Similarity	NPC248638
0.9371	High Similarity	NPC197168
0.9371	High Similarity	NPC475985
0.9367	High Similarity	NPC474351
0.9367	High Similarity	NPC266314
0.9367	High Similarity	NPC134783
0.9367	High Similarity	NPC475883
0.9367	High Similarity	NPC474187
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC473990
0.9363	High Similarity	NPC250214
0.9321	High Similarity	NPC472276
0.9321	High Similarity	NPC103307
0.9313	High Similarity	NPC473286
0.9313	High Similarity	NPC224280
0.9313	High Similarity	NPC62261
0.9313	High Similarity	NPC234052
0.9313	High Similarity	NPC472277
0.9308	High Similarity	NPC229632
0.9308	High Similarity	NPC474150
0.9308	High Similarity	NPC52204
0.9308	High Similarity	NPC474162
0.9308	High Similarity	NPC220912
0.9308	High Similarity	NPC469575
0.9308	High Similarity	NPC25152
0.9304	High Similarity	NPC472624
0.9304	High Similarity	NPC228785
0.9304	High Similarity	NPC174953
0.9304	High Similarity	NPC14353
0.9304	High Similarity	NPC56085
0.9299	High Similarity	NPC36852
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC262286
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC472910
0.9299	High Similarity	NPC472911
0.9299	High Similarity	NPC245758
0.9299	High Similarity	NPC96167
0.9299	High Similarity	NPC284820
0.9299	High Similarity	NPC156057
0.9299	High Similarity	NPC472913
0.9299	High Similarity	NPC473272
0.9299	High Similarity	NPC78225
0.9299	High Similarity	NPC162869
0.9299	High Similarity	NPC472914
0.9299	High Similarity	NPC222814
0.9295	High Similarity	NPC200761
0.9295	High Similarity	NPC226025
0.9295	High Similarity	NPC255807
0.9295	High Similarity	NPC31018
0.9295	High Similarity	NPC470327
0.9295	High Similarity	NPC45849
0.9295	High Similarity	NPC477503
0.9286	High Similarity	NPC338131
0.9259	High Similarity	NPC326877
0.9259	High Similarity	NPC288813
0.9259	High Similarity	NPC177480
0.9255	High Similarity	NPC472452
0.9255	High Similarity	NPC235610
0.925	High Similarity	NPC7483
0.925	High Similarity	NPC41301
0.925	High Similarity	NPC205265
0.925	High Similarity	NPC124038
0.925	High Similarity	NPC472281
0.9245	High Similarity	NPC471211
0.9245	High Similarity	NPC278052
0.9245	High Similarity	NPC228383
0.9245	High Similarity	NPC472632
0.9245	High Similarity	NPC471210
0.9245	High Similarity	NPC61010
0.9245	High Similarity	NPC165549
0.9245	High Similarity	NPC40491
0.9245	High Similarity	NPC471212
0.9241	High Similarity	NPC100123
0.9236	High Similarity	NPC470328
0.9236	High Similarity	NPC138243
0.9236	High Similarity	NPC235165
0.9236	High Similarity	NPC68093
0.9236	High Similarity	NPC278778
0.9236	High Similarity	NPC35038
0.9236	High Similarity	NPC191146
0.9236	High Similarity	NPC255106
0.9236	High Similarity	NPC291878
0.9236	High Similarity	NPC472626
0.9236	High Similarity	NPC195796
0.9236	High Similarity	NPC209614
0.9231	High Similarity	NPC280937
0.9231	High Similarity	NPC472915
0.9226	High Similarity	NPC117579
0.9222	High Similarity	NPC150977
0.9212	High Similarity	NPC156635
0.9207	High Similarity	NPC310794
0.9202	High Similarity	NPC279209
0.9202	High Similarity	NPC102277
0.9198	High Similarity	NPC8965
0.9193	High Similarity	NPC300053
0.9193	High Similarity	NPC275780
0.9193	High Similarity	NPC108433
0.9193	High Similarity	NPC239752
0.9193	High Similarity	NPC37183
0.9193	High Similarity	NPC293319
0.9193	High Similarity	NPC472450
0.9187	High Similarity	NPC83922
0.9187	High Similarity	NPC472402
0.9187	High Similarity	NPC472448
0.9187	High Similarity	NPC472635
0.9187	High Similarity	NPC474034
0.9187	High Similarity	NPC474033
0.9182	High Similarity	NPC200746
0.9182	High Similarity	NPC320359
0.9182	High Similarity	NPC192686
0.9182	High Similarity	NPC471976
0.9182	High Similarity	NPC119209
0.9182	High Similarity	NPC36217
0.9182	High Similarity	NPC118256
0.9182	High Similarity	NPC204290
0.9182	High Similarity	NPC299436
0.9182	High Similarity	NPC475784
0.9177	High Similarity	NPC471209
0.9177	High Similarity	NPC474055
0.9177	High Similarity	NPC476981
0.9177	High Similarity	NPC129684
0.9177	High Similarity	NPC241904
0.9177	High Similarity	NPC99597
0.9177	High Similarity	NPC27337
0.9177	High Similarity	NPC210084
0.9177	High Similarity	NPC300727
0.9177	High Similarity	NPC299520
0.9177	High Similarity	NPC196448
0.9177	High Similarity	NPC291508
0.9177	High Similarity	NPC472598
0.9177	High Similarity	NPC19097
0.9172	High Similarity	NPC113906
0.9167	High Similarity	NPC106976
0.9161	High Similarity	NPC179183
0.9157	High Similarity	NPC246877
0.9136	High Similarity	NPC472449
0.9136	High Similarity	NPC39091
0.9136	High Similarity	NPC277480
0.9136	High Similarity	NPC119589
0.913	High Similarity	NPC146134
0.913	High Similarity	NPC474350
0.913	High Similarity	NPC23298
0.913	High Similarity	NPC189473
0.913	High Similarity	NPC186686
0.913	High Similarity	NPC220313
0.913	High Similarity	NPC236132
0.9125	High Similarity	NPC474038
0.9125	High Similarity	NPC167678
0.9125	High Similarity	NPC40037
0.9125	High Similarity	NPC3629
0.9125	High Similarity	NPC26326
0.9125	High Similarity	NPC29876
0.9125	High Similarity	NPC66288
0.9125	High Similarity	NPC173137
0.9125	High Similarity	NPC472275
0.9119	High Similarity	NPC476242
0.9119	High Similarity	NPC152904
0.9119	High Similarity	NPC329091
0.9119	High Similarity	NPC469658
0.9114	High Similarity	NPC274730
0.9114	High Similarity	NPC472916
0.9114	High Similarity	NPC142339
0.9108	High Similarity	NPC74924
0.9108	High Similarity	NPC298692
0.9108	High Similarity	NPC192083

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 NPC273959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	927
0.2-0.3	1787
0.3-0.4	2587
0.4-0.5	1813
0.5-0.6	996
0.6-0.7	478
0.7-0.8	150
0.8-0.85	34
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9551	High Similarity	NPD5494	Approved
0.9108	High Similarity	NPD2393	Clinical (unspecified phase)
0.9045	High Similarity	NPD1934	Approved
0.8987	High Similarity	NPD2801	Approved
0.8841	High Similarity	NPD6168	Clinical (unspecified phase)
0.8841	High Similarity	NPD6166	Phase 2
0.8841	High Similarity	NPD6167	Clinical (unspecified phase)
0.8758	High Similarity	NPD3882	Suspended
0.8631	High Similarity	NPD7074	Phase 3
0.8623	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD5844	Phase 1
0.8571	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD4380	Phase 2
0.8545	High Similarity	NPD6959	Discontinued
0.8528	High Similarity	NPD4868	Clinical (unspecified phase)
0.8521	High Similarity	NPD7472	Approved
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7473	Discontinued
0.8418	Intermediate Similarity	NPD1511	Approved
0.8387	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6232	Discontinued
0.8372	Intermediate Similarity	NPD7808	Phase 3
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8363	Intermediate Similarity	NPD6797	Phase 2
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8323	Intermediate Similarity	NPD1247	Approved
0.8314	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD7819	Suspended
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD7411	Suspended
0.8165	Intermediate Similarity	NPD2800	Approved
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2534	Approved
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2533	Approved
0.8137	Intermediate Similarity	NPD2532	Approved
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8089	Intermediate Similarity	NPD2796	Approved
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8024	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.7988	Intermediate Similarity	NPD919	Approved
0.7965	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3749	Approved
0.7904	Intermediate Similarity	NPD37	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7875	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7228	Approved
0.787	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD4965	Approved
0.787	Intermediate Similarity	NPD7768	Phase 2
0.787	Intermediate Similarity	NPD4967	Phase 2
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD6799	Approved
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1607	Approved
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7753	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7669	Intermediate Similarity	NPD3750	Approved
0.7658	Intermediate Similarity	NPD943	Approved
0.7658	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1613	Approved
0.7644	Intermediate Similarity	NPD5710	Approved
0.7644	Intermediate Similarity	NPD5711	Approved
0.7643	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6099	Approved
0.764	Intermediate Similarity	NPD6100	Approved
0.7611	Intermediate Similarity	NPD8312	Approved
0.7611	Intermediate Similarity	NPD8313	Approved
0.7607	Intermediate Similarity	NPD1243	Approved
0.7607	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5403	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2344	Approved
0.759	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7564	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6651	Approved
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.753	Intermediate Similarity	NPD7390	Discontinued
0.753	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7515	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD447	Suspended
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.747	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2861	Phase 2
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.7443	Intermediate Similarity	NPD7229	Phase 3
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6782	Approved
0.741	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD8150	Discontinued
0.7385	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3748	Approved
0.736	Intermediate Similarity	NPD2403	Approved
0.7353	Intermediate Similarity	NPD1653	Approved
0.7326	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD7783	Phase 2
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7302	Intermediate Similarity	NPD4361	Phase 2
0.7302	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5353	Approved
0.729	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD1933	Approved
0.7283	Intermediate Similarity	NPD6844	Discontinued
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD5242	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5124	Phase 1
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.7173	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6823	Phase 2
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7136	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7126	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD9494	Approved
0.7107	Intermediate Similarity	NPD7584	Approved
0.7099	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3268	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4749	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7874	Approved
0.7083	Intermediate Similarity	NPD2654	Approved
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD2798	Approved
0.7062	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.7041	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD4287	Approved
0.7035	Intermediate Similarity	NPD6273	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7026	Intermediate Similarity	NPD2494	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