NPASS Compound

Structure

CID308689 OpenBabel06191716112D 22 23 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 1.7321 1.0000 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 -1.7321 -3.0000 0.0000 C 0 0 0 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 1 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 14 20 1 1 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.14
Volume:	319.477
LogP:	3.288
LogD:	2.771
LogS:	-3.587
# Rotatable Bonds:	6
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	2.923
Fsp3:	0.222
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:	-4.629
MDCK Permeability:	5.325978690962074e-06
Pgp-inhibitor:	0.147
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	98.20897674560547%
Volume Distribution (VD):	0.554
Pgp-substrate:	1.6580926179885864%

ADMET: Metabolism

CYP1A2-inhibitor:	0.854
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.39
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.829
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	14.014
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.543
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.885
Carcinogencity:	0.462
Eye Corrosion:	0.003
Eye Irritation:	0.522
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC308689

Natural Product ID:	NPC308689
*Common Name:**	Magnolignan A
IUPAC Name:	(2R)-3-[4-hydroxy-3-(2-hydroxy-5-prop-2-enylphenyl)phenyl]propane-1,2-diol
Synonyms:	Magnolignan A
Standard InCHIKey:	ORPULAPYNPMMAQ-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C18H20O4/c1-2-3-12-4-6-17(21)15(9-12)16-10-13(5-7-18(16)22)8-14(20)11-19/h2,4-7,9-10,14,19-22H,1,3,8,11H2/t14-/m1/s1
SMILES:	C=CCc1ccc(c(c1)c1cc(ccc1O)C[C@H](CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346748
PubChem CID:	11066525
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	Wood	n.a.	n.a.	PMID[7119806]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28043	Streblus asper	Species	Moraceae	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	3
Others	1

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	1000000.0	nM	PMID[456459]
NPT27	Others	Unspecified		CC50	=	176430.0	nM	PMID[456459]

☑ 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 NPC308689 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	300
0.1-0.2	1374
0.2-0.3	3873
0.3-0.4	12314
0.4-0.5	7189
0.5-0.6	8279
0.6-0.7	7052
0.7-0.8	2075
0.8-0.85	174
0.85-0.9	56
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC44732
0.9717	High Similarity	NPC12656
0.9717	High Similarity	NPC473137
0.9709	High Similarity	NPC262365
0.932	High Similarity	NPC288411
0.9231	High Similarity	NPC138942
0.9223	High Similarity	NPC168829
0.8942	High Similarity	NPC40258
0.8942	High Similarity	NPC7686
0.8942	High Similarity	NPC91461
0.8938	High Similarity	NPC182240
0.8932	High Similarity	NPC78119
0.8932	High Similarity	NPC132078
0.8932	High Similarity	NPC51333
0.8932	High Similarity	NPC216468
0.886	High Similarity	NPC223451
0.886	High Similarity	NPC473136
0.8846	High Similarity	NPC213730
0.8818	High Similarity	NPC228988
0.8818	High Similarity	NPC228425
0.8807	High Similarity	NPC174096
0.8807	High Similarity	NPC79793
0.8807	High Similarity	NPC296683
0.8807	High Similarity	NPC147634
0.8807	High Similarity	NPC226401
0.8807	High Similarity	NPC120982
0.8803	High Similarity	NPC231767
0.8785	High Similarity	NPC54765
0.8774	High Similarity	NPC323810
0.875	High Similarity	NPC128723
0.875	High Similarity	NPC474486
0.8729	High Similarity	NPC127975
0.8727	High Similarity	NPC257430
0.8727	High Similarity	NPC179002
0.8727	High Similarity	NPC187583
0.8716	High Similarity	NPC62258
0.8716	High Similarity	NPC55617
0.8707	High Similarity	NPC31936
0.8667	High Similarity	NPC294741
0.8661	High Similarity	NPC120280
0.8649	High Similarity	NPC286222
0.8636	High Similarity	NPC475018
0.8624	High Similarity	NPC95344
0.8611	High Similarity	NPC271274
0.8609	High Similarity	NPC151197
0.8571	High Similarity	NPC35344
0.8571	High Similarity	NPC141003
0.8559	High Similarity	NPC95716
0.8558	High Similarity	NPC82664
0.8558	High Similarity	NPC216520
0.8558	High Similarity	NPC132271
0.8558	High Similarity	NPC292730
0.8544	High Similarity	NPC128062
0.8544	High Similarity	NPC151715
0.8534	High Similarity	NPC475245
0.8519	High Similarity	NPC233396
0.8519	High Similarity	NPC154899
0.8509	High Similarity	NPC308828
0.8491	Intermediate Similarity	NPC225506
0.8482	Intermediate Similarity	NPC46940
0.8476	Intermediate Similarity	NPC77492
0.8468	Intermediate Similarity	NPC132720
0.8462	Intermediate Similarity	NPC26244
0.8447	Intermediate Similarity	NPC271440
0.844	Intermediate Similarity	NPC92623
0.844	Intermediate Similarity	NPC135464
0.8435	Intermediate Similarity	NPC477136
0.8435	Intermediate Similarity	NPC299180
0.8421	Intermediate Similarity	NPC147179
0.8411	Intermediate Similarity	NPC471578
0.8411	Intermediate Similarity	NPC101025
0.8407	Intermediate Similarity	NPC471485
0.8396	Intermediate Similarity	NPC122005
0.8396	Intermediate Similarity	NPC252821
0.8396	Intermediate Similarity	NPC92730
0.8381	Intermediate Similarity	NPC473388
0.8378	Intermediate Similarity	NPC473524
0.8378	Intermediate Similarity	NPC254833
0.8378	Intermediate Similarity	NPC228343
0.8378	Intermediate Similarity	NPC58865
0.8374	Intermediate Similarity	NPC143483
0.8362	Intermediate Similarity	NPC469609
0.835	Intermediate Similarity	NPC45040
0.8349	Intermediate Similarity	NPC99557
0.8349	Intermediate Similarity	NPC219286
0.8348	Intermediate Similarity	NPC38893
0.8348	Intermediate Similarity	NPC219112
0.8348	Intermediate Similarity	NPC301651
0.8348	Intermediate Similarity	NPC308311
0.8348	Intermediate Similarity	NPC92
0.8348	Intermediate Similarity	NPC473556
0.8348	Intermediate Similarity	NPC477137
0.8348	Intermediate Similarity	NPC469663
0.8333	Intermediate Similarity	NPC268160
0.8319	Intermediate Similarity	NPC43525
0.8304	Intermediate Similarity	NPC63345
0.8302	Intermediate Similarity	NPC225464
0.8302	Intermediate Similarity	NPC474073
0.8291	Intermediate Similarity	NPC469644
0.8288	Intermediate Similarity	NPC61885
0.8288	Intermediate Similarity	NPC233835
0.8288	Intermediate Similarity	NPC63698
0.8286	Intermediate Similarity	NPC274678
0.8286	Intermediate Similarity	NPC8392
0.8276	Intermediate Similarity	NPC476266
0.8269	Intermediate Similarity	NPC138117
0.8269	Intermediate Similarity	NPC325292
0.8261	Intermediate Similarity	NPC35797
0.8261	Intermediate Similarity	NPC192948
0.8257	Intermediate Similarity	NPC471511
0.8257	Intermediate Similarity	NPC475225
0.8252	Intermediate Similarity	NPC300017
0.8246	Intermediate Similarity	NPC715
0.8246	Intermediate Similarity	NPC261343
0.8241	Intermediate Similarity	NPC51015
0.8241	Intermediate Similarity	NPC12221
0.8235	Intermediate Similarity	NPC251259
0.823	Intermediate Similarity	NPC177576
0.823	Intermediate Similarity	NPC476632
0.823	Intermediate Similarity	NPC4493
0.823	Intermediate Similarity	NPC225679
0.823	Intermediate Similarity	NPC165770
0.823	Intermediate Similarity	NPC151537
0.822	Intermediate Similarity	NPC472071
0.8214	Intermediate Similarity	NPC314187
0.8211	Intermediate Similarity	NPC471064
0.8211	Intermediate Similarity	NPC472968
0.8205	Intermediate Similarity	NPC471671
0.8198	Intermediate Similarity	NPC151477
0.819	Intermediate Similarity	NPC474358
0.819	Intermediate Similarity	NPC257540
0.819	Intermediate Similarity	NPC137496
0.819	Intermediate Similarity	NPC474387
0.819	Intermediate Similarity	NPC247858
0.819	Intermediate Similarity	NPC76938
0.819	Intermediate Similarity	NPC261973
0.819	Intermediate Similarity	NPC154511
0.8182	Intermediate Similarity	NPC239291
0.8182	Intermediate Similarity	NPC474839
0.8174	Intermediate Similarity	NPC195922
0.8174	Intermediate Similarity	NPC107240
0.8173	Intermediate Similarity	NPC204210
0.8167	Intermediate Similarity	NPC471794
0.8165	Intermediate Similarity	NPC235762
0.8165	Intermediate Similarity	NPC471228
0.8165	Intermediate Similarity	NPC233827
0.8165	Intermediate Similarity	NPC108497
0.8158	Intermediate Similarity	NPC290353
0.8158	Intermediate Similarity	NPC153795
0.8158	Intermediate Similarity	NPC302371
0.8158	Intermediate Similarity	NPC42911
0.8151	Intermediate Similarity	NPC131868
0.8148	Intermediate Similarity	NPC174911
0.8142	Intermediate Similarity	NPC321252
0.8142	Intermediate Similarity	NPC252544
0.8142	Intermediate Similarity	NPC13482
0.8136	Intermediate Similarity	NPC109371
0.8136	Intermediate Similarity	NPC470215
0.8136	Intermediate Similarity	NPC470214
0.8131	Intermediate Similarity	NPC32674
0.8131	Intermediate Similarity	NPC156313
0.813	Intermediate Similarity	NPC21563
0.8125	Intermediate Similarity	NPC11554
0.812	Intermediate Similarity	NPC304510
0.812	Intermediate Similarity	NPC470760
0.812	Intermediate Similarity	NPC145023
0.812	Intermediate Similarity	NPC172219
0.812	Intermediate Similarity	NPC277588
0.812	Intermediate Similarity	NPC175799
0.812	Intermediate Similarity	NPC200988
0.812	Intermediate Similarity	NPC610
0.812	Intermediate Similarity	NPC320864
0.8115	Intermediate Similarity	NPC81641
0.8113	Intermediate Similarity	NPC313650
0.8113	Intermediate Similarity	NPC32714
0.8113	Intermediate Similarity	NPC144682
0.8108	Intermediate Similarity	NPC248904
0.8099	Intermediate Similarity	NPC473451
0.8099	Intermediate Similarity	NPC474160
0.8091	Intermediate Similarity	NPC238696
0.8091	Intermediate Similarity	NPC119860
0.8087	Intermediate Similarity	NPC123175
0.8087	Intermediate Similarity	NPC176730
0.8087	Intermediate Similarity	NPC322239
0.8087	Intermediate Similarity	NPC117846
0.8083	Intermediate Similarity	NPC295034
0.8083	Intermediate Similarity	NPC475166
0.8083	Intermediate Similarity	NPC237667
0.8073	Intermediate Similarity	NPC110764
0.8067	Intermediate Similarity	NPC34634
0.8067	Intermediate Similarity	NPC260832
0.8067	Intermediate Similarity	NPC265454
0.8067	Intermediate Similarity	NPC135467
0.8065	Intermediate Similarity	NPC148366
0.8065	Intermediate Similarity	NPC311293
0.8058	Intermediate Similarity	NPC104216
0.8053	Intermediate Similarity	NPC306045
0.8053	Intermediate Similarity	NPC265211
0.8053	Intermediate Similarity	NPC474272
0.8051	Intermediate Similarity	NPC86198

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 NPC308689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	863
0.2-0.3	1401
0.3-0.4	2861
0.4-0.5	1927
0.5-0.6	1167
0.6-0.7	556
0.7-0.8	86
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD3020	Approved
0.8462	Intermediate Similarity	NPD2860	Approved
0.8462	Intermediate Similarity	NPD2859	Approved
0.8378	Intermediate Similarity	NPD3021	Approved
0.8378	Intermediate Similarity	NPD3022	Approved
0.8365	Intermediate Similarity	NPD2933	Approved
0.8365	Intermediate Similarity	NPD2934	Approved
0.8158	Intermediate Similarity	NPD7635	Approved
0.8113	Intermediate Similarity	NPD1809	Phase 2
0.8095	Intermediate Similarity	NPD845	Approved
0.8036	Intermediate Similarity	NPD2342	Discontinued
0.8019	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD3094	Phase 2
0.7934	Intermediate Similarity	NPD3092	Approved
0.7931	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD3091	Approved
0.7818	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD844	Approved
0.7748	Intermediate Similarity	NPD940	Approved
0.7748	Intermediate Similarity	NPD846	Approved
0.7706	Intermediate Similarity	NPD288	Approved
0.7679	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4060	Phase 1
0.7623	Intermediate Similarity	NPD3095	Discontinued
0.7623	Intermediate Similarity	NPD4589	Approved
0.7603	Intermediate Similarity	NPD5304	Approved
0.7603	Intermediate Similarity	NPD5303	Approved
0.7597	Intermediate Similarity	NPD6405	Approved
0.7597	Intermediate Similarity	NPD6407	Approved
0.7578	Intermediate Similarity	NPD3027	Phase 3
0.7559	Intermediate Similarity	NPD2861	Phase 2
0.7519	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD111	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.748	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD2286	Discontinued
0.7479	Intermediate Similarity	NPD2229	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7438	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4750	Phase 3
0.7426	Intermediate Similarity	NPD3400	Discontinued
0.7417	Intermediate Similarity	NPD497	Approved
0.7405	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1613	Approved
0.7395	Intermediate Similarity	NPD7843	Approved
0.7364	Intermediate Similarity	NPD4908	Phase 1
0.736	Intermediate Similarity	NPD1610	Phase 2
0.7353	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD495	Approved
0.7333	Intermediate Similarity	NPD496	Approved
0.7333	Intermediate Similarity	NPD5283	Phase 1
0.7333	Intermediate Similarity	NPD498	Approved
0.7328	Intermediate Similarity	NPD968	Approved
0.7323	Intermediate Similarity	NPD8651	Approved
0.7288	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3061	Approved
0.7273	Intermediate Similarity	NPD3062	Approved
0.7273	Intermediate Similarity	NPD3059	Approved
0.7266	Intermediate Similarity	NPD1164	Approved
0.7266	Intermediate Similarity	NPD4103	Phase 2
0.7266	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD290	Approved
0.7258	Intermediate Similarity	NPD4093	Discontinued
0.7244	Intermediate Similarity	NPD4659	Approved
0.7239	Intermediate Similarity	NPD4536	Approved
0.7239	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4538	Approved
0.7222	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6355	Discontinued
0.7213	Intermediate Similarity	NPD6671	Approved
0.7206	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9384	Approved
0.72	Intermediate Similarity	NPD5846	Approved
0.72	Intermediate Similarity	NPD4626	Approved
0.72	Intermediate Similarity	NPD3019	Approved
0.72	Intermediate Similarity	NPD4059	Approved
0.72	Intermediate Similarity	NPD6516	Phase 2
0.72	Intermediate Similarity	NPD2932	Approved
0.72	Intermediate Similarity	NPD9381	Approved
0.7185	Intermediate Similarity	NPD5588	Approved
0.7185	Intermediate Similarity	NPD5960	Phase 3
0.7177	Intermediate Similarity	NPD7330	Discontinued
0.7177	Intermediate Similarity	NPD1548	Phase 1
0.7167	Intermediate Similarity	NPD228	Approved
0.7165	Intermediate Similarity	NPD2561	Approved
0.7165	Intermediate Similarity	NPD2562	Approved
0.7164	Intermediate Similarity	NPD5314	Approved
0.7154	Intermediate Similarity	NPD5736	Approved
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7132	Intermediate Similarity	NPD1131	Approved
0.7132	Intermediate Similarity	NPD1135	Approved
0.7132	Intermediate Similarity	NPD1133	Approved
0.7132	Intermediate Similarity	NPD1134	Approved
0.7132	Intermediate Similarity	NPD1129	Approved
0.7131	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6798	Discontinued
0.7111	Intermediate Similarity	NPD3553	Approved
0.7111	Intermediate Similarity	NPD3555	Approved
0.7111	Intermediate Similarity	NPD3554	Approved
0.7111	Intermediate Similarity	NPD3552	Approved
0.7099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1091	Approved
0.7063	Intermediate Similarity	NPD5126	Approved
0.7063	Intermediate Similarity	NPD5125	Phase 3
0.7045	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD1444	Approved
0.7034	Intermediate Similarity	NPD1445	Approved
0.7029	Intermediate Similarity	NPD2424	Discontinued
0.7023	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5451	Approved
0.6992	Remote Similarity	NPD9618	Approved
0.6992	Remote Similarity	NPD9614	Approved
0.6984	Remote Similarity	NPD5691	Approved
0.6984	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1651	Approved
0.6977	Remote Similarity	NPD9622	Approved
0.6977	Remote Similarity	NPD6582	Phase 2
0.6977	Remote Similarity	NPD6583	Phase 3
0.6977	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1669	Approved
0.6972	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD9379	Approved
0.6967	Remote Similarity	NPD9377	Approved
0.6966	Remote Similarity	NPD4380	Phase 2
0.6963	Remote Similarity	NPD5735	Approved
0.696	Remote Similarity	NPD16	Approved
0.696	Remote Similarity	NPD856	Approved
0.6957	Remote Similarity	NPD7266	Discontinued
0.6953	Remote Similarity	NPD1201	Approved
0.6947	Remote Similarity	NPD3690	Phase 2
0.6947	Remote Similarity	NPD3691	Phase 2
0.6947	Remote Similarity	NPD6584	Phase 3
0.6942	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6663	Approved
0.6935	Remote Similarity	NPD6387	Discontinued
0.6929	Remote Similarity	NPD2667	Approved
0.6929	Remote Similarity	NPD4535	Phase 3
0.6929	Remote Similarity	NPD2668	Approved
0.6929	Remote Similarity	NPD1751	Approved
0.6923	Remote Similarity	NPD5310	Approved
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD5311	Approved
0.6912	Remote Similarity	NPD2568	Approved
0.6905	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7041	Phase 2
0.6899	Remote Similarity	NPD2231	Phase 2
0.6899	Remote Similarity	NPD2232	Approved
0.6899	Remote Similarity	NPD2233	Approved
0.6899	Remote Similarity	NPD2235	Phase 2
0.6899	Remote Similarity	NPD2230	Approved
0.6894	Remote Similarity	NPD4208	Discontinued
0.6893	Remote Similarity	NPD9294	Approved
0.6889	Remote Similarity	NPD2238	Phase 2
0.6889	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5405	Approved
0.6884	Remote Similarity	NPD5408	Approved
0.6884	Remote Similarity	NPD5404	Approved
0.6884	Remote Similarity	NPD5406	Approved
0.6875	Remote Similarity	NPD3847	Discontinued
0.6875	Remote Similarity	NPD3421	Phase 3
0.6875	Remote Similarity	NPD3143	Discontinued
0.687	Remote Similarity	NPD1470	Approved
0.687	Remote Similarity	NPD3055	Approved
0.687	Remote Similarity	NPD3053	Approved
0.687	Remote Similarity	NPD9273	Approved
0.6866	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD9610	Approved
0.6855	Remote Similarity	NPD2629	Approved
0.6853	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD5763	Approved
0.6831	Remote Similarity	NPD5058	Phase 3
0.6829	Remote Similarity	NPD5535	Approved
0.6829	Remote Similarity	NPD1138	Approved
0.6825	Remote Similarity	NPD9615	Approved
0.6825	Remote Similarity	NPD318	Approved
0.6825	Remote Similarity	NPD9616	Approved
0.6825	Remote Similarity	NPD9613	Approved
0.6825	Remote Similarity	NPD317	Approved
0.6824	Remote Similarity	NPD8455	Phase 2
0.6822	Remote Similarity	NPD1611	Approved
0.6818	Remote Similarity	NPD9620	Approved
0.6818	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD9619	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