NPASS Compound

Structure

NPC473309 OpenBabel07101719252D 38 41 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 -3.4641 1.0000 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 -1.7321 0.0000 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 0.8660 2.5000 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 -0.8660 2.5000 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 -5.1962 0.0000 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 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 -0.8660 1.5000 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 -2.5981 4.5000 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 -3.4641 0.0000 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 -0.8660 -0.5000 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 4.0000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 3 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 -1.7321 4.0000 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 -6.0622 1.5000 0.0000 O 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 1 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 7 2 0 0 0 0 4 21 1 0 0 0 0 5 12 1 0 0 0 0 5 21 2 0 0 0 0 6 13 2 0 0 0 0 6 21 1 0 0 0 0 7 24 1 0 0 0 0 8 14 2 0 0 0 0 8 23 1 0 0 0 0 9 15 1 0 0 0 0 9 22 2 0 0 0 0 10 16 2 0 0 0 0 10 22 1 0 0 0 0 11 17 1 0 0 0 0 11 23 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 31 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 22 29 1 0 0 0 0 23 31 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 32 1 0 0 0 0 30 32 2 0 0 0 0 30 35 1 0 0 0 0 31 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.22
Volume:	546.27
LogP:	6.118
LogD:	4.4
LogS:	-4.583
# Rotatable Bonds:	10
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	3.116
Fsp3:	0.188
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.433
MDCK Permeability:	1.1560201528482139e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.104
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.4
30% Bioavailability (F30%):	0.385

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	100.89677429199219%
Volume Distribution (VD):	0.732
Pgp-substrate:	0.6639817953109741%

ADMET: Metabolism

CYP1A2-inhibitor:	0.303
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.838
CYP2C9-substrate:	0.99
CYP2D6-inhibitor:	0.623
CYP2D6-substrate:	0.968
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	8.289
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.559
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.521
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.956
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.63

Download Data

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

Natural Product: NPC473309

Natural Product ID:	NPC473309
*Common Name:**	Cochinchinenene B
IUPAC Name:	2-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-methoxyphenyl)propyl]-3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenol
Synonyms:	cochinchinenene B
Standard InCHIKey:	XZVDYCHPJWUZFS-QPJJXVBHSA-N
Standard InCHI:	InChI=1S/C32H32O6/c1-36-27-15-9-22(10-16-27)29(17-11-23-8-14-26(34)19-31(23)38-3)32-24(18-28(37-2)20-30(32)35)7-4-21-5-12-25(33)13-6-21/h4-10,12-16,18-20,29,33-35H,11,17H2,1-3H3/b7-4+
SMILES:	COC1=CC=C(C=C1)C(CCC2=C(C=C(C=C2)O)OC)C3=C(C=C(C=C3O)OC)C=CC4=CC=C(C=C4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399481
PubChem CID:	23655936
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
MIC	1

Activity Type	# Activity
Individual Protein	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1592	Individual Protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	>	39100.0	nM	PMID[532793]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	62500.0	nM	PMID[532793]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	17800.0	nM	PMID[532793]

☑ 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 NPC473309 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	407
0.1-0.2	1730
0.2-0.3	4065
0.3-0.4	12914
0.4-0.5	5559
0.5-0.6	4296
0.6-0.7	8190
0.7-0.8	4535
0.8-0.85	659
0.85-0.9	245
0.9-0.95	81
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC471519
0.9839	High Similarity	NPC471518
0.9683	High Similarity	NPC471517
0.9603	High Similarity	NPC254000
0.9516	High Similarity	NPC113495
0.9375	High Similarity	NPC282508
0.9248	High Similarity	NPC273623
0.9248	High Similarity	NPC472090
0.9248	High Similarity	NPC472091
0.9248	High Similarity	NPC472092
0.9242	High Similarity	NPC472646
0.9242	High Similarity	NPC71465
0.9237	High Similarity	NPC37410
0.9237	High Similarity	NPC15109
0.9237	High Similarity	NPC11727
0.9237	High Similarity	NPC258780
0.9231	High Similarity	NPC469610
0.9225	High Similarity	NPC8899
0.9179	High Similarity	NPC472089
0.9167	High Similarity	NPC170328
0.9167	High Similarity	NPC472649
0.9167	High Similarity	NPC472647
0.9167	High Similarity	NPC206525
0.9167	High Similarity	NPC133463
0.9167	High Similarity	NPC191462
0.9167	High Similarity	NPC472648
0.9154	High Similarity	NPC469611
0.9134	High Similarity	NPC170485
0.9113	High Similarity	NPC102639
0.9111	High Similarity	NPC472087
0.9111	High Similarity	NPC472088
0.9077	High Similarity	NPC238168
0.9077	High Similarity	NPC237424
0.9062	High Similarity	NPC473221
0.9023	High Similarity	NPC471522
0.9015	High Similarity	NPC476617
0.9015	High Similarity	NPC476616
0.9015	High Similarity	NPC476615
0.8992	High Similarity	NPC215300
0.8984	High Similarity	NPC82299
0.8976	High Similarity	NPC228503
0.8976	High Similarity	NPC138248
0.8963	High Similarity	NPC174787
0.8963	High Similarity	NPC182509
0.8963	High Similarity	NPC213607
0.8955	High Similarity	NPC470308
0.8955	High Similarity	NPC470307
0.8947	High Similarity	NPC125579
0.8915	High Similarity	NPC53781
0.8913	High Similarity	NPC149633
0.8906	High Similarity	NPC278955
0.8906	High Similarity	NPC105718
0.8906	High Similarity	NPC105031
0.8889	High Similarity	NPC476633
0.8881	High Similarity	NPC141717
0.8872	High Similarity	NPC473107
0.8846	High Similarity	NPC38017
0.8832	High Similarity	NPC183709
0.8832	High Similarity	NPC277784
0.8806	High Similarity	NPC313081
0.8794	High Similarity	NPC476969
0.879	High Similarity	NPC127894
0.879	High Similarity	NPC15860
0.879	High Similarity	NPC470759
0.879	High Similarity	NPC219070
0.879	High Similarity	NPC33270
0.879	High Similarity	NPC474933
0.879	High Similarity	NPC69261
0.8788	High Similarity	NPC472590
0.8788	High Similarity	NPC15543
0.8786	High Similarity	NPC133209
0.8786	High Similarity	NPC231712
0.8786	High Similarity	NPC112819
0.8786	High Similarity	NPC6702
0.8786	High Similarity	NPC111134
0.8786	High Similarity	NPC242774
0.8786	High Similarity	NPC262297
0.8786	High Similarity	NPC237546
0.8786	High Similarity	NPC224921
0.8768	High Similarity	NPC173203
0.8768	High Similarity	NPC163508
0.875	High Similarity	NPC55947
0.8714	High Similarity	NPC71686
0.8714	High Similarity	NPC176804
0.8712	High Similarity	NPC126836
0.871	High Similarity	NPC203113
0.871	High Similarity	NPC85292
0.871	High Similarity	NPC150624
0.871	High Similarity	NPC229147
0.871	High Similarity	NPC141090
0.871	High Similarity	NPC114064
0.871	High Similarity	NPC54507
0.8705	High Similarity	NPC304894
0.8705	High Similarity	NPC15659
0.8692	High Similarity	NPC283049
0.8692	High Similarity	NPC50315
0.8692	High Similarity	NPC230479
0.8692	High Similarity	NPC26879
0.8676	High Similarity	NPC266006
0.8672	High Similarity	NPC120172
0.8667	High Similarity	NPC158142
0.8667	High Similarity	NPC200557
0.8667	High Similarity	NPC10314
0.8667	High Similarity	NPC69029
0.8667	High Similarity	NPC294884
0.8667	High Similarity	NPC108198
0.8662	High Similarity	NPC148516
0.8662	High Similarity	NPC177172
0.8662	High Similarity	NPC180605
0.8662	High Similarity	NPC107862
0.8662	High Similarity	NPC122980
0.8652	High Similarity	NPC153182
0.8652	High Similarity	NPC174251
0.8651	High Similarity	NPC184302
0.8647	High Similarity	NPC474238
0.864	High Similarity	NPC50521
0.864	High Similarity	NPC195466
0.864	High Similarity	NPC221549
0.864	High Similarity	NPC244816
0.8636	High Similarity	NPC222108
0.8636	High Similarity	NPC96719
0.8636	High Similarity	NPC93962
0.8633	High Similarity	NPC469630
0.8629	High Similarity	NPC808
0.8629	High Similarity	NPC185541
0.8629	High Similarity	NPC53906
0.8629	High Similarity	NPC464
0.8615	High Similarity	NPC105925
0.8613	High Similarity	NPC184613
0.8613	High Similarity	NPC220344
0.8613	High Similarity	NPC243996
0.8613	High Similarity	NPC132804
0.8613	High Similarity	NPC275061
0.8603	High Similarity	NPC205442
0.8603	High Similarity	NPC202846
0.8603	High Similarity	NPC143139
0.8601	High Similarity	NPC218801
0.8593	High Similarity	NPC125649
0.8593	High Similarity	NPC209199
0.8593	High Similarity	NPC256307
0.8593	High Similarity	NPC66840
0.8583	High Similarity	NPC69006
0.8582	High Similarity	NPC126291
0.8582	High Similarity	NPC303144
0.8582	High Similarity	NPC161958
0.8582	High Similarity	NPC14468
0.8582	High Similarity	NPC14224
0.8582	High Similarity	NPC274454
0.8582	High Similarity	NPC215678
0.8571	High Similarity	NPC224157
0.8571	High Similarity	NPC131118
0.8571	High Similarity	NPC190514
0.8571	High Similarity	NPC192687
0.8561	High Similarity	NPC38664
0.8561	High Similarity	NPC53986
0.8551	High Similarity	NPC22317
0.8551	High Similarity	NPC12668
0.8551	High Similarity	NPC308768
0.855	High Similarity	NPC223953
0.8548	High Similarity	NPC22610
0.8548	High Similarity	NPC180508
0.8548	High Similarity	NPC228287
0.8548	High Similarity	NPC276737
0.8542	High Similarity	NPC233886
0.8542	High Similarity	NPC157081
0.8542	High Similarity	NPC105073
0.8542	High Similarity	NPC224528
0.854	High Similarity	NPC266453
0.854	High Similarity	NPC242715
0.854	High Similarity	NPC230919
0.854	High Similarity	NPC22902
0.854	High Similarity	NPC56329
0.854	High Similarity	NPC200935
0.8538	High Similarity	NPC97578
0.8531	High Similarity	NPC321657
0.8531	High Similarity	NPC318373
0.8529	High Similarity	NPC241241
0.8529	High Similarity	NPC472370
0.8529	High Similarity	NPC111655
0.8527	High Similarity	NPC74137
0.8527	High Similarity	NPC77789
0.8527	High Similarity	NPC18128
0.8519	High Similarity	NPC32778
0.8507	High Similarity	NPC118683
0.8507	High Similarity	NPC293203
0.8507	High Similarity	NPC164804
0.8507	High Similarity	NPC211413
0.8507	High Similarity	NPC244888
0.8507	High Similarity	NPC68205
0.8496	Intermediate Similarity	NPC474227
0.8496	Intermediate Similarity	NPC190144
0.8485	Intermediate Similarity	NPC236791
0.8485	Intermediate Similarity	NPC124452
0.8485	Intermediate Similarity	NPC169474
0.8485	Intermediate Similarity	NPC82679
0.8485	Intermediate Similarity	NPC246620
0.8485	Intermediate Similarity	NPC74817
0.8485	Intermediate Similarity	NPC324112
0.8485	Intermediate Similarity	NPC127587
0.8485	Intermediate Similarity	NPC46978

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 NPC473309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	1007
0.2-0.3	1435
0.3-0.4	2746
0.4-0.5	1801
0.5-0.6	1048
0.6-0.7	611
0.7-0.8	132
0.8-0.85	7
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8992	High Similarity	NPD4908	Phase 1
0.8855	High Similarity	NPD4907	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD1610	Phase 2
0.8358	Intermediate Similarity	NPD4625	Phase 3
0.8182	Intermediate Similarity	NPD4749	Approved
0.8182	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD1548	Phase 1
0.8134	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD3027	Phase 3
0.8029	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD2861	Phase 2
0.7941	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1613	Approved
0.7914	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD7447	Phase 1
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7762	Intermediate Similarity	NPD6099	Approved
0.7762	Intermediate Similarity	NPD6100	Approved
0.7755	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7041	Phase 2
0.7717	Intermediate Similarity	NPD4750	Phase 3
0.7712	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD3018	Phase 2
0.7676	Intermediate Similarity	NPD4097	Suspended
0.7671	Intermediate Similarity	NPD3750	Approved
0.766	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7213	Phase 3
0.7635	Intermediate Similarity	NPD7212	Phase 2
0.7615	Intermediate Similarity	NPD5283	Phase 1
0.7581	Intermediate Similarity	NPD846	Approved
0.7581	Intermediate Similarity	NPD940	Approved
0.758	Intermediate Similarity	NPD6959	Discontinued
0.7551	Intermediate Similarity	NPD3892	Phase 2
0.7551	Intermediate Similarity	NPD7466	Approved
0.7534	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7518	Intermediate Similarity	NPD2982	Phase 2
0.7518	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD6671	Approved
0.7483	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6584	Phase 3
0.7482	Intermediate Similarity	NPD4624	Approved
0.7481	Intermediate Similarity	NPD4626	Approved
0.7468	Intermediate Similarity	NPD37	Approved
0.7455	Intermediate Similarity	NPD8053	Approved
0.7455	Intermediate Similarity	NPD8054	Approved
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7445	Intermediate Similarity	NPD2981	Phase 2
0.7442	Intermediate Similarity	NPD5451	Approved
0.7432	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7229	Phase 3
0.7421	Intermediate Similarity	NPD6232	Discontinued
0.7419	Intermediate Similarity	NPD3020	Approved
0.7415	Intermediate Similarity	NPD7037	Approved
0.7413	Intermediate Similarity	NPD1240	Approved
0.7413	Intermediate Similarity	NPD2238	Phase 2
0.7391	Intermediate Similarity	NPD5327	Phase 3
0.7361	Intermediate Similarity	NPD5124	Phase 1
0.7361	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5735	Approved
0.7358	Intermediate Similarity	NPD7199	Phase 2
0.7351	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6234	Discontinued
0.7338	Intermediate Similarity	NPD8651	Approved
0.7338	Intermediate Similarity	NPD6696	Suspended
0.7333	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3748	Approved
0.7329	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4965	Approved
0.7325	Intermediate Similarity	NPD4966	Approved
0.7325	Intermediate Similarity	NPD4967	Phase 2
0.7319	Intermediate Similarity	NPD2233	Approved
0.7319	Intermediate Similarity	NPD2230	Approved
0.7319	Intermediate Similarity	NPD2232	Approved
0.7315	Intermediate Similarity	NPD7003	Approved
0.731	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD3021	Approved
0.7308	Intermediate Similarity	NPD3022	Approved
0.7292	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3620	Phase 2
0.7287	Intermediate Similarity	NPD2342	Discontinued
0.7285	Intermediate Similarity	NPD7390	Discontinued
0.7278	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7635	Approved
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6583	Phase 3
0.7266	Intermediate Similarity	NPD6582	Phase 2
0.7248	Intermediate Similarity	NPD6674	Discontinued
0.7239	Intermediate Similarity	NPD8252	Approved
0.7239	Intermediate Similarity	NPD7228	Approved
0.7239	Intermediate Similarity	NPD709	Approved
0.7239	Intermediate Similarity	NPD8251	Approved
0.7239	Intermediate Similarity	NPD8099	Discontinued
0.723	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1283	Approved
0.7206	Intermediate Similarity	NPD3091	Approved
0.7203	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD228	Approved
0.7195	Intermediate Similarity	NPD5844	Phase 1
0.7195	Intermediate Similarity	NPD8156	Discontinued
0.7192	Intermediate Similarity	NPD6353	Approved
0.7181	Intermediate Similarity	NPD1549	Phase 2
0.7179	Intermediate Similarity	NPD7411	Suspended
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7172	Intermediate Similarity	NPD4140	Approved
0.7163	Intermediate Similarity	NPD2797	Approved
0.7163	Intermediate Similarity	NPD3094	Phase 2
0.7163	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5405	Approved
0.7162	Intermediate Similarity	NPD2935	Discontinued
0.7162	Intermediate Similarity	NPD5406	Approved
0.7162	Intermediate Similarity	NPD5404	Approved
0.7162	Intermediate Similarity	NPD5408	Approved
0.7161	Intermediate Similarity	NPD4005	Discontinued
0.7153	Intermediate Similarity	NPD1651	Approved
0.7153	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD7843	Approved
0.7134	Intermediate Similarity	NPD1934	Approved
0.7124	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3092	Approved
0.7117	Intermediate Similarity	NPD6166	Phase 2
0.7117	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4380	Phase 2
0.7114	Intermediate Similarity	NPD3540	Phase 1
0.7114	Intermediate Similarity	NPD5763	Approved
0.7114	Intermediate Similarity	NPD5762	Approved
0.7111	Intermediate Similarity	NPD7157	Approved
0.7105	Intermediate Similarity	NPD7124	Phase 2
0.7101	Intermediate Similarity	NPD2668	Approved
0.7101	Intermediate Similarity	NPD2667	Approved
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7095	Intermediate Similarity	NPD4108	Discontinued
0.7089	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD2801	Approved
0.708	Intermediate Similarity	NPD7741	Discontinued
0.7075	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1511	Approved
0.7059	Intermediate Similarity	NPD7340	Approved
0.7051	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3539	Phase 1
0.7047	Intermediate Similarity	NPD2796	Approved
0.7034	Intermediate Similarity	NPD6798	Discontinued
0.7034	Intermediate Similarity	NPD3268	Approved
0.7034	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD4093	Discontinued
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2532	Approved
0.7013	Intermediate Similarity	NPD2534	Approved
0.7013	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2533	Approved
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3705	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1281	Approved
0.6986	Remote Similarity	NPD8032	Phase 2
0.6985	Remote Similarity	NPD6387	Discontinued
0.6984	Remote Similarity	NPD288	Approved
0.698	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3095	Discontinued
0.6978	Remote Similarity	NPD3019	Approved
0.6978	Remote Similarity	NPD4059	Approved
0.6978	Remote Similarity	NPD6516	Phase 2
0.6978	Remote Similarity	NPD5846	Approved
0.6975	Remote Similarity	NPD6746	Phase 2
0.6972	Remote Similarity	NPD3225	Approved
0.6972	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2684	Approved
0.6968	Remote Similarity	NPD1512	Approved
0.6957	Remote Similarity	NPD4055	Discovery
0.6957	Remote Similarity	NPD7075	Discontinued
0.6951	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD968	Approved
0.6944	Remote Similarity	NPD5736	Approved
0.6943	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3847	Discontinued
0.6928	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7549	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