NPASS Compound

Structure

CID266197 OpenBabel06191716072D 39 41 0 0 1 0 0 0 0 0999 V2000 2.5981 -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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 2.5981 1.5000 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 1.7321 -0.0000 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 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 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 1.7321 1.0000 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -4.3301 1.5000 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 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 2 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 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 37 1 0 0 0 0 7 38 1 0 0 0 0 8 10 2 0 0 0 0 8 21 1 0 0 0 0 9 11 2 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 21 2 0 0 0 0 14 26 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 22 1 0 0 0 0 16 29 2 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 1 0 0 0 20 30 1 0 0 0 0 20 39 1 0 0 0 0 23 30 1 0 0 0 0 24 26 2 0 0 0 0 24 32 1 0 0 0 0 25 27 2 0 0 0 0 25 33 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 31 2 0 0 0 0 28 37 1 0 0 0 0 29 31 1 0 0 0 0 29 38 1 0 0 0 0 30 34 1 1 0 0 0 31 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.27
Volume:	565.656
LogP:	4.935
LogD:	4.222
LogS:	-4.941
# Rotatable Bonds:	13
TPSA:	106.84
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	3.781
Fsp3:	0.419
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	3.381990609341301e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.395

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	90.12208557128906%
Volume Distribution (VD):	0.604
Pgp-substrate:	8.082342147827148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.324
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	11.181
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.701
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.217
Skin Sensitization:	0.906
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC266197

Natural Product ID:	NPC266197
*Common Name:**	(+)-(7''s,8S,8'r,8''r)-4,4''-Dihydroxy-3,3',3'',5'-Tetramethoxy-4',8''-Oxy-8,8'-Sesquineolignan-7''-Ol
IUPAC Name:	4-[(2S,3R)-4-[4-[(1S,2R)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-2,3-dimethylbutyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	SXBVVAJDHDRCBF-YFKFKODSSA-N
Standard InCHI:	InChI=1S/C31H40O8/c1-18(12-21-8-10-24(32)26(14-21)35-4)19(2)13-22-15-28(37-6)31(29(16-22)38-7)39-20(3)30(34)23-9-11-25(33)27(17-23)36-5/h8-11,14-20,30,32-34H,12-13H2,1-7H3/t18-,19+,20+,30+/m0/s1
SMILES:	C[C@@H](Cc1ccc(c(c1)OC)O)[C@H](C)Cc1cc(c(c(c1)OC)O[C@H](C)[C@H](c1ccc(c(c1)OC)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812646
PubChem CID:	53344594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	2520.0	nM	PMID[558841]

☑ 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 NPC266197 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	432
0.1-0.2	1458
0.2-0.3	4100
0.3-0.4	11210
0.4-0.5	7367
0.5-0.6	4155
0.6-0.7	6473
0.7-0.8	5519
0.8-0.85	977
0.85-0.9	712
0.9-0.95	282
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC291101
0.9774	High Similarity	NPC22517
0.9706	High Similarity	NPC470097
0.9706	High Similarity	NPC471415
0.9706	High Similarity	NPC114119
0.9565	High Similarity	NPC317053
0.9565	High Similarity	NPC260397
0.9565	High Similarity	NPC324492
0.9496	High Similarity	NPC328567
0.9496	High Similarity	NPC320671
0.9496	High Similarity	NPC320970
0.9496	High Similarity	NPC327412
0.9485	High Similarity	NPC178054
0.9478	High Similarity	NPC77861
0.9474	High Similarity	NPC170694
0.947	High Similarity	NPC184447
0.947	High Similarity	NPC470752
0.947	High Similarity	NPC35932
0.947	High Similarity	NPC16208
0.947	High Similarity	NPC7903
0.947	High Similarity	NPC160991
0.9407	High Similarity	NPC474390
0.9394	High Similarity	NPC470095
0.9394	High Similarity	NPC309787
0.9394	High Similarity	NPC474017
0.9394	High Similarity	NPC472597
0.9394	High Similarity	NPC469613
0.9394	High Similarity	NPC470096
0.9394	High Similarity	NPC30043
0.9394	High Similarity	NPC469625
0.9362	High Similarity	NPC470826
0.9362	High Similarity	NPC473266
0.9362	High Similarity	NPC470098
0.9353	High Similarity	NPC181615
0.9343	High Similarity	NPC471389
0.9333	High Similarity	NPC162659
0.9333	High Similarity	NPC265433
0.9333	High Similarity	NPC270456
0.9333	High Similarity	NPC306441
0.9333	High Similarity	NPC248727
0.9333	High Similarity	NPC16435
0.9328	High Similarity	NPC287745
0.9328	High Similarity	NPC326095
0.9328	High Similarity	NPC310854
0.9328	High Similarity	NPC244983
0.9323	High Similarity	NPC201587
0.9323	High Similarity	NPC253105
0.9318	High Similarity	NPC472338
0.9318	High Similarity	NPC469614
0.9318	High Similarity	NPC469612
0.9296	High Similarity	NPC477612
0.927	High Similarity	NPC309124
0.927	High Similarity	NPC262189
0.927	High Similarity	NPC184797
0.927	High Similarity	NPC22317
0.9259	High Similarity	NPC260898
0.9259	High Similarity	NPC234333
0.9259	High Similarity	NPC94750
0.9259	High Similarity	NPC474206
0.9259	High Similarity	NPC47398
0.9259	High Similarity	NPC121812
0.9259	High Similarity	NPC61946
0.9259	High Similarity	NPC112246
0.9259	High Similarity	NPC470356
0.9259	High Similarity	NPC93783
0.9259	High Similarity	NPC112939
0.9254	High Similarity	NPC158331
0.9254	High Similarity	NPC475840
0.9242	High Similarity	NPC285339
0.9242	High Similarity	NPC470258
0.9242	High Similarity	NPC3439
0.9242	High Similarity	NPC190629
0.9242	High Similarity	NPC218856
0.9242	High Similarity	NPC202582
0.9242	High Similarity	NPC170844
0.9242	High Similarity	NPC210623
0.9242	High Similarity	NPC222004
0.9242	High Similarity	NPC226788
0.9242	High Similarity	NPC476968
0.9242	High Similarity	NPC273295
0.9231	High Similarity	NPC324517
0.9231	High Similarity	NPC321972
0.9231	High Similarity	NPC329343
0.9225	High Similarity	NPC211561
0.922	High Similarity	NPC39657
0.9209	High Similarity	NPC469630
0.9203	High Similarity	NPC311530
0.9203	High Similarity	NPC470372
0.9203	High Similarity	NPC87725
0.9203	High Similarity	NPC263261
0.9197	High Similarity	NPC473739
0.9197	High Similarity	NPC471388
0.9197	High Similarity	NPC232164
0.9197	High Similarity	NPC236306
0.9197	High Similarity	NPC260741
0.9197	High Similarity	NPC127218
0.9197	High Similarity	NPC319647
0.9197	High Similarity	NPC25966
0.9197	High Similarity	NPC70682
0.9197	High Similarity	NPC245207
0.9191	High Similarity	NPC472334
0.9191	High Similarity	NPC302701
0.9191	High Similarity	NPC474639
0.9191	High Similarity	NPC230734
0.9191	High Similarity	NPC269091
0.9191	High Similarity	NPC472336
0.9191	High Similarity	NPC227503
0.9185	High Similarity	NPC317380
0.9185	High Similarity	NPC478085
0.9179	High Similarity	NPC175067
0.9179	High Similarity	NPC204215
0.9167	High Similarity	NPC186843
0.9167	High Similarity	NPC206615
0.9167	High Similarity	NPC98631
0.9167	High Similarity	NPC470213
0.9143	High Similarity	NPC171932
0.9143	High Similarity	NPC25292
0.9143	High Similarity	NPC473045
0.9143	High Similarity	NPC28440
0.9137	High Similarity	NPC472714
0.9137	High Similarity	NPC107161
0.9137	High Similarity	NPC5262
0.9137	High Similarity	NPC189115
0.9137	High Similarity	NPC469559
0.913	High Similarity	NPC254759
0.913	High Similarity	NPC160283
0.913	High Similarity	NPC55793
0.9124	High Similarity	NPC326797
0.9124	High Similarity	NPC211549
0.9124	High Similarity	NPC102904
0.9124	High Similarity	NPC103976
0.9124	High Similarity	NPC474282
0.9124	High Similarity	NPC107551
0.9124	High Similarity	NPC276490
0.9124	High Similarity	NPC176051
0.9118	High Similarity	NPC126409
0.9118	High Similarity	NPC34103
0.9118	High Similarity	NPC151224
0.9118	High Similarity	NPC164787
0.9118	High Similarity	NPC165155
0.9118	High Similarity	NPC24490
0.9118	High Similarity	NPC472337
0.9118	High Similarity	NPC99572
0.9118	High Similarity	NPC141765
0.9111	High Similarity	NPC11060
0.9111	High Similarity	NPC168059
0.9111	High Similarity	NPC229442
0.9111	High Similarity	NPC263064
0.9103	High Similarity	NPC470769
0.9098	High Similarity	NPC5851
0.9098	High Similarity	NPC86030
0.9091	High Similarity	NPC210355
0.9091	High Similarity	NPC163332
0.9091	High Similarity	NPC292056
0.9091	High Similarity	NPC183181
0.9091	High Similarity	NPC111247
0.9091	High Similarity	NPC118787
0.9091	High Similarity	NPC51328
0.9091	High Similarity	NPC470699
0.9091	High Similarity	NPC474119
0.9091	High Similarity	NPC127587
0.9091	High Similarity	NPC319625
0.9091	High Similarity	NPC147821
0.9091	High Similarity	NPC165045
0.9091	High Similarity	NPC118533
0.9091	High Similarity	NPC55158
0.9091	High Similarity	NPC41706
0.9091	High Similarity	NPC286235
0.9085	High Similarity	NPC263940
0.9085	High Similarity	NPC204770
0.9085	High Similarity	NPC236202
0.9085	High Similarity	NPC108811
0.9085	High Similarity	NPC170103
0.9085	High Similarity	NPC82917
0.9085	High Similarity	NPC58190
0.9085	High Similarity	NPC202742
0.9085	High Similarity	NPC18185
0.9085	High Similarity	NPC262911
0.9085	High Similarity	NPC294558
0.9085	High Similarity	NPC70409
0.9078	High Similarity	NPC475096
0.9071	High Similarity	NPC473044
0.9071	High Similarity	NPC477616
0.9065	High Similarity	NPC469661
0.9065	High Similarity	NPC35216
0.9065	High Similarity	NPC247291
0.9058	High Similarity	NPC292882
0.9058	High Similarity	NPC230124
0.9058	High Similarity	NPC55947
0.9058	High Similarity	NPC184613
0.9058	High Similarity	NPC6300
0.9058	High Similarity	NPC114171
0.9058	High Similarity	NPC260842
0.9051	High Similarity	NPC471719
0.9051	High Similarity	NPC173660
0.9051	High Similarity	NPC470802
0.9051	High Similarity	NPC234952
0.9037	High Similarity	NPC131128
0.9037	High Similarity	NPC126029
0.9037	High Similarity	NPC127624

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 NPC266197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	851
0.2-0.3	1836
0.3-0.4	2650
0.4-0.5	1710
0.5-0.6	927
0.6-0.7	628
0.7-0.8	173
0.8-0.85	9
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9242	High Similarity	NPD3027	Phase 3
0.9037	High Similarity	NPD1613	Approved
0.9037	High Similarity	NPD1612	Clinical (unspecified phase)
0.8741	High Similarity	NPD1529	Clinical (unspecified phase)
0.8667	High Similarity	NPD1530	Clinical (unspecified phase)
0.8603	High Similarity	NPD4908	Phase 1
0.8478	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD1610	Phase 2
0.8165	Intermediate Similarity	NPD6166	Phase 2
0.8165	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1934	Approved
0.8077	Intermediate Similarity	NPD6234	Discontinued
0.8065	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7987	Intermediate Similarity	NPD37	Approved
0.7975	Intermediate Similarity	NPD7199	Phase 2
0.7972	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3620	Phase 2
0.7971	Intermediate Similarity	NPD2982	Phase 2
0.7971	Intermediate Similarity	NPD2983	Phase 2
0.7961	Intermediate Similarity	NPD1653	Approved
0.7958	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD5283	Phase 1
0.795	Intermediate Similarity	NPD7228	Approved
0.7949	Intermediate Similarity	NPD4965	Approved
0.7949	Intermediate Similarity	NPD4967	Phase 2
0.7949	Intermediate Similarity	NPD4966	Approved
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1548	Phase 1
0.7905	Intermediate Similarity	NPD6674	Discontinued
0.7899	Intermediate Similarity	NPD2981	Phase 2
0.7872	Intermediate Similarity	NPD3018	Phase 2
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.7842	Intermediate Similarity	NPD4749	Approved
0.7836	Intermediate Similarity	NPD7157	Approved
0.7821	Intermediate Similarity	NPD2801	Approved
0.7803	Intermediate Similarity	NPD228	Approved
0.7791	Intermediate Similarity	NPD7054	Approved
0.777	Intermediate Similarity	NPD7266	Discontinued
0.7764	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4625	Phase 3
0.7744	Intermediate Similarity	NPD7843	Approved
0.7744	Intermediate Similarity	NPD7472	Approved
0.773	Intermediate Similarity	NPD3818	Discontinued
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7671	Intermediate Similarity	NPD5735	Approved
0.7667	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3021	Approved
0.7652	Intermediate Similarity	NPD3022	Approved
0.761	Intermediate Similarity	NPD3882	Suspended
0.7603	Intermediate Similarity	NPD4060	Phase 1
0.7603	Intermediate Similarity	NPD1558	Phase 1
0.759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1511	Approved
0.7576	Intermediate Similarity	NPD2684	Approved
0.7568	Intermediate Similarity	NPD4538	Approved
0.7568	Intermediate Similarity	NPD4536	Approved
0.7568	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7473	Discontinued
0.7554	Intermediate Similarity	NPD6516	Phase 2
0.7554	Intermediate Similarity	NPD5846	Approved
0.7552	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6584	Phase 3
0.7547	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3817	Phase 2
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7535	Intermediate Similarity	NPD8651	Approved
0.7532	Intermediate Similarity	NPD7447	Phase 1
0.7517	Intermediate Similarity	NPD7095	Approved
0.7516	Intermediate Similarity	NPD4675	Approved
0.7516	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD1512	Approved
0.7468	Intermediate Similarity	NPD7213	Phase 3
0.7468	Intermediate Similarity	NPD7212	Phase 2
0.7466	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4005	Discontinued
0.7451	Intermediate Similarity	NPD6190	Approved
0.7447	Intermediate Similarity	NPD1091	Approved
0.7447	Intermediate Similarity	NPD3705	Approved
0.744	Intermediate Similarity	NPD7240	Approved
0.7415	Intermediate Similarity	NPD6233	Phase 2
0.7412	Intermediate Similarity	NPD8053	Approved
0.7412	Intermediate Similarity	NPD8054	Approved
0.7405	Intermediate Similarity	NPD4380	Phase 2
0.7403	Intermediate Similarity	NPD7124	Phase 2
0.74	Intermediate Similarity	NPD5588	Approved
0.74	Intermediate Similarity	NPD5960	Phase 3
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7549	Discontinued
0.7386	Intermediate Similarity	NPD6331	Phase 2
0.7375	Intermediate Similarity	NPD1465	Phase 2
0.7365	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5494	Approved
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6099	Approved
0.7351	Intermediate Similarity	NPD6100	Approved
0.7347	Intermediate Similarity	NPD6798	Discontinued
0.7346	Intermediate Similarity	NPD7075	Discontinued
0.7346	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6582	Phase 2
0.7343	Intermediate Similarity	NPD5327	Phase 3
0.7343	Intermediate Similarity	NPD6583	Phase 3
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3060	Approved
0.732	Intermediate Similarity	NPD1652	Phase 2
0.732	Intermediate Similarity	NPD5177	Phase 3
0.7319	Intermediate Similarity	NPD6671	Approved
0.7317	Intermediate Similarity	NPD8127	Discontinued
0.7315	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5124	Phase 1
0.7315	Intermediate Similarity	NPD6355	Discontinued
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5762	Approved
0.7303	Intermediate Similarity	NPD3540	Phase 1
0.7303	Intermediate Similarity	NPD5763	Approved
0.7303	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5058	Phase 3
0.7273	Intermediate Similarity	NPD3892	Phase 2
0.7273	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD7466	Approved
0.7267	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7267	Intermediate Similarity	NPD6653	Approved
0.7261	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7526	Approved
0.7261	Intermediate Similarity	NPD52	Approved
0.7248	Intermediate Similarity	NPD2238	Phase 2
0.7248	Intermediate Similarity	NPD4140	Approved
0.7241	Intermediate Similarity	NPD3094	Phase 2
0.7239	Intermediate Similarity	NPD290	Approved
0.7237	Intermediate Similarity	NPD3539	Phase 1
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7234	Intermediate Similarity	NPD1357	Approved
0.7233	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2677	Approved
0.7222	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7097	Phase 1
0.7219	Intermediate Similarity	NPD6111	Discontinued
0.7212	Intermediate Similarity	NPD6959	Discontinued
0.7211	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4162	Approved
0.7208	Intermediate Similarity	NPD4237	Approved
0.7208	Intermediate Similarity	NPD4236	Phase 3
0.7203	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4123	Phase 3
0.719	Intermediate Similarity	NPD1375	Discontinued
0.719	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7906	Approved
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7171	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7164	Intermediate Similarity	NPD968	Approved
0.7161	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7819	Suspended
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7152	Intermediate Similarity	NPD6353	Approved
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD4357	Discontinued
0.7126	Intermediate Similarity	NPD4663	Approved
0.7124	Intermediate Similarity	NPD2161	Phase 2
0.7121	Intermediate Similarity	NPD291	Approved
0.7117	Intermediate Similarity	NPD5402	Approved
0.7115	Intermediate Similarity	NPD5241	Discontinued
0.7111	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5535	Approved
0.7099	Intermediate Similarity	NPD6801	Discontinued
0.7092	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD3657	Discovery
0.7083	Intermediate Similarity	NPD3092	Approved
0.7083	Intermediate Similarity	NPD27	Approved
0.7083	Intermediate Similarity	NPD2489	Approved
0.7066	Intermediate Similarity	NPD3787	Discontinued

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