NPASS Compound

Structure

CID317380 OpenBabel06191716142D 21 23 0 0 1 0 0 0 0 0999 V2000 1.7321 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 -3.4641 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 -5.1962 0.0000 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 3.0000 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 -1.7321 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 3 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 -5.1962 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 -0.0000 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 -6.0622 1.5000 0.0000 O 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	296.261
LogP:	3.308
LogD:	3.195
LogS:	-3.18
# Rotatable Bonds:	3
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.911
Synthetic Accessibility Score:	2.877
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.665
MDCK Permeability:	2.1657770048477687e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	97.42973327636719%
Volume Distribution (VD):	0.71
Pgp-substrate:	1.559139370918274%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.272
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.59
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	15.39
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.618
Skin Sensitization:	0.95
Carcinogencity:	0.779
Eye Corrosion:	0.004
Eye Irritation:	0.922
Respiratory Toxicity:	0.192

Download Data

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

Natural Product: NPC317380

Natural Product ID:	NPC317380
*Common Name:**	7-Hydroxy-3-(4-Hydroxybenzyl)-8-Methoxychroman
IUPAC Name:	3-[(4-hydroxyphenyl)methyl]-8-methoxy-3,4-dihydro-2H-chromen-7-ol
Synonyms:
Standard InCHIKey:	CPKWBZLDPWJFPM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-20-17-15(19)7-4-13-9-12(10-21-16(13)17)8-11-2-5-14(18)6-3-11/h2-7,12,18-19H,8-10H2,1H3
SMILES:	COc1c(O)ccc2c1OCC(C2)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398848
PubChem CID:	44445077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO495	Daemonorops draco	Species	Arecaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	55900.0	nM	PMID[485515]

☑ 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 NPC317380 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	1671
0.2-0.3	4996
0.3-0.4	13005
0.4-0.5	4644
0.5-0.6	4042
0.6-0.7	6185
0.7-0.8	5676
0.8-0.85	1055
0.85-0.9	652
0.9-0.95	289
0.95-1	64

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC265433
0.9845	High Similarity	NPC162659
0.9845	High Similarity	NPC248727
0.9845	High Similarity	NPC270456
0.9769	High Similarity	NPC276490
0.9767	High Similarity	NPC94750
0.9767	High Similarity	NPC474206
0.9767	High Similarity	NPC470356
0.9767	High Similarity	NPC121812
0.9767	High Similarity	NPC112939
0.9767	High Similarity	NPC112246
0.9695	High Similarity	NPC70682
0.9695	High Similarity	NPC127218
0.9695	High Similarity	NPC319647
0.9695	High Similarity	NPC25966
0.9695	High Similarity	NPC245207
0.9695	High Similarity	NPC260741
0.9692	High Similarity	NPC16435
0.9692	High Similarity	NPC306441
0.9692	High Similarity	NPC230734
0.9692	High Similarity	NPC474639
0.9692	High Similarity	NPC227503
0.9688	High Similarity	NPC86655
0.9688	High Similarity	NPC127624
0.9688	High Similarity	NPC202762
0.9621	High Similarity	NPC309124
0.9621	High Similarity	NPC184797
0.9618	High Similarity	NPC211549
0.9618	High Similarity	NPC176051
0.9618	High Similarity	NPC474282
0.9618	High Similarity	NPC107551
0.9618	High Similarity	NPC102904
0.9618	High Similarity	NPC103976
0.9618	High Similarity	NPC326797
0.9615	High Similarity	NPC61946
0.9615	High Similarity	NPC47398
0.9615	High Similarity	NPC151224
0.9615	High Similarity	NPC195022
0.9615	High Similarity	NPC234333
0.9615	High Similarity	NPC260898
0.9612	High Similarity	NPC475840
0.9612	High Similarity	NPC11060
0.9612	High Similarity	NPC229442
0.9612	High Similarity	NPC168059
0.9549	High Similarity	NPC35216
0.9549	High Similarity	NPC471389
0.9545	High Similarity	NPC232164
0.9545	High Similarity	NPC236306
0.9545	High Similarity	NPC473739
0.9542	High Similarity	NPC302701
0.9542	High Similarity	NPC173660
0.9542	High Similarity	NPC269091
0.9538	High Similarity	NPC478085
0.9531	High Similarity	NPC91291
0.9478	High Similarity	NPC204347
0.9478	High Similarity	NPC59841
0.9478	High Similarity	NPC475891
0.9478	High Similarity	NPC107161
0.9478	High Similarity	NPC2613
0.9474	High Similarity	NPC259519
0.9466	High Similarity	NPC164787
0.9466	High Similarity	NPC473413
0.9462	High Similarity	NPC263064
0.9449	High Similarity	NPC74817
0.9449	High Similarity	NPC169474
0.9449	High Similarity	NPC159968
0.9449	High Similarity	NPC82679
0.9449	High Similarity	NPC210355
0.9449	High Similarity	NPC293054
0.9449	High Similarity	NPC282000
0.9449	High Similarity	NPC246620
0.9449	High Similarity	NPC324112
0.9449	High Similarity	NPC236791
0.9449	High Similarity	NPC124452
0.9403	High Similarity	NPC247291
0.9398	High Similarity	NPC471388
0.9394	High Similarity	NPC470802
0.9394	High Similarity	NPC234952
0.9394	High Similarity	NPC472336
0.9394	High Similarity	NPC472334
0.9389	High Similarity	NPC106215
0.9389	High Similarity	NPC170694
0.9385	High Similarity	NPC15658
0.9385	High Similarity	NPC201587
0.9385	High Similarity	NPC126029
0.9385	High Similarity	NPC261619
0.9385	High Similarity	NPC253105
0.9385	High Similarity	NPC185604
0.9385	High Similarity	NPC61477
0.9385	High Similarity	NPC78770
0.9385	High Similarity	NPC219876
0.938	High Similarity	NPC472338
0.9375	High Similarity	NPC226331
0.9375	High Similarity	NPC46274
0.937	High Similarity	NPC78974
0.937	High Similarity	NPC18924
0.937	High Similarity	NPC214406
0.937	High Similarity	NPC44748
0.937	High Similarity	NPC103823
0.937	High Similarity	NPC223136
0.937	High Similarity	NPC28730
0.9338	High Similarity	NPC280092
0.9338	High Similarity	NPC45257
0.9338	High Similarity	NPC12641
0.9338	High Similarity	NPC93323
0.9338	High Similarity	NPC473108
0.9328	High Similarity	NPC22317
0.9328	High Similarity	NPC254759
0.9328	High Similarity	NPC160283
0.9328	High Similarity	NPC27495
0.9318	High Similarity	NPC472337
0.9313	High Similarity	NPC36661
0.9308	High Similarity	NPC268266
0.9308	High Similarity	NPC472597
0.9308	High Similarity	NPC268342
0.9308	High Similarity	NPC220825
0.9308	High Similarity	NPC42760
0.9302	High Similarity	NPC212015
0.9297	High Similarity	NPC5447
0.9297	High Similarity	NPC470699
0.9297	High Similarity	NPC250432
0.9297	High Similarity	NPC127587
0.9291	High Similarity	NPC116907
0.9291	High Similarity	NPC221077
0.9291	High Similarity	NPC57490
0.9291	High Similarity	NPC251855
0.9291	High Similarity	NPC82483
0.9291	High Similarity	NPC208950
0.9291	High Similarity	NPC472093
0.9291	High Similarity	NPC234400
0.9291	High Similarity	NPC60885
0.9291	High Similarity	NPC203133
0.9291	High Similarity	NPC298757
0.9291	High Similarity	NPC193544
0.9291	High Similarity	NPC117214
0.9291	High Similarity	NPC475169
0.9291	High Similarity	NPC265483
0.9291	High Similarity	NPC17943
0.9291	High Similarity	NPC299584
0.9291	High Similarity	NPC233410
0.9291	High Similarity	NPC105925
0.9265	High Similarity	NPC85264
0.9265	High Similarity	NPC47633
0.9265	High Similarity	NPC81638
0.9265	High Similarity	NPC102044
0.9259	High Similarity	NPC263261
0.9259	High Similarity	NPC178054
0.9259	High Similarity	NPC87725
0.9254	High Similarity	NPC292882
0.9254	High Similarity	NPC32630
0.9242	High Similarity	NPC256307
0.9242	High Similarity	NPC66840
0.9237	High Similarity	NPC35932
0.9237	High Similarity	NPC160991
0.9237	High Similarity	NPC470752
0.9237	High Similarity	NPC6451
0.9237	High Similarity	NPC184447
0.9237	High Similarity	NPC7903
0.9237	High Similarity	NPC16208
0.9231	High Similarity	NPC234488
0.9231	High Similarity	NPC299221
0.9231	High Similarity	NPC214860
0.9231	High Similarity	NPC51840
0.9231	High Similarity	NPC126836
0.9231	High Similarity	NPC311680
0.9225	High Similarity	NPC186843
0.9225	High Similarity	NPC28765
0.9225	High Similarity	NPC154866
0.9225	High Similarity	NPC31707
0.9225	High Similarity	NPC98631
0.9225	High Similarity	NPC470213
0.9225	High Similarity	NPC206615
0.9219	High Similarity	NPC181361
0.9219	High Similarity	NPC76451
0.9213	High Similarity	NPC228972
0.9213	High Similarity	NPC122792
0.9203	High Similarity	NPC87794
0.9203	High Similarity	NPC211758
0.9197	High Similarity	NPC50250
0.9197	High Similarity	NPC63879
0.9197	High Similarity	NPC469795
0.9185	High Similarity	NPC266197
0.9185	High Similarity	NPC291101
0.9179	High Similarity	NPC94994
0.9173	High Similarity	NPC313081
0.9173	High Similarity	NPC134968
0.9167	High Similarity	NPC158331
0.916	High Similarity	NPC12275
0.916	High Similarity	NPC309787
0.916	High Similarity	NPC474017
0.916	High Similarity	NPC232275
0.916	High Similarity	NPC474356
0.916	High Similarity	NPC45715
0.9154	High Similarity	NPC222004
0.9154	High Similarity	NPC10225
0.9154	High Similarity	NPC5851
0.9154	High Similarity	NPC470258
0.9154	High Similarity	NPC45824
0.9154	High Similarity	NPC469951
0.9154	High Similarity	NPC218856

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 NPC317380 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	933
0.2-0.3	1817
0.3-0.4	2716
0.4-0.5	1592
0.5-0.6	876
0.6-0.7	658
0.7-0.8	172
0.8-0.85	14
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9385	High Similarity	NPD1612	Clinical (unspecified phase)
0.9385	High Similarity	NPD1613	Approved
0.9375	High Similarity	NPD1529	Clinical (unspecified phase)
0.9297	High Similarity	NPD1530	Clinical (unspecified phase)
0.9154	High Similarity	NPD3027	Phase 3
0.8931	High Similarity	NPD4908	Phase 1
0.8828	High Similarity	NPD1610	Phase 2
0.8797	High Similarity	NPD4907	Clinical (unspecified phase)
0.8516	High Similarity	NPD1548	Phase 1
0.8503	High Similarity	NPD1934	Approved
0.8409	Intermediate Similarity	NPD4749	Approved
0.8322	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD4625	Phase 3
0.8296	Intermediate Similarity	NPD2861	Phase 2
0.8296	Intermediate Similarity	NPD3018	Phase 2
0.8248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2801	Approved
0.8134	Intermediate Similarity	NPD2982	Phase 2
0.8134	Intermediate Similarity	NPD2983	Phase 2
0.8125	Intermediate Similarity	NPD5283	Phase 1
0.811	Intermediate Similarity	NPD228	Approved
0.8108	Intermediate Similarity	NPD1653	Approved
0.8092	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD3882	Suspended
0.8077	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6166	Phase 2
0.8077	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD2981	Phase 2
0.8	Intermediate Similarity	NPD4060	Phase 1
0.7959	Intermediate Similarity	NPD1511	Approved
0.7885	Intermediate Similarity	NPD7199	Phase 2
0.7875	Intermediate Similarity	NPD7074	Phase 3
0.7872	Intermediate Similarity	NPD1558	Phase 1
0.7871	Intermediate Similarity	NPD6234	Discontinued
0.7868	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1512	Approved
0.7812	Intermediate Similarity	NPD3021	Approved
0.7812	Intermediate Similarity	NPD3022	Approved
0.7812	Intermediate Similarity	NPD7054	Approved
0.7808	Intermediate Similarity	NPD6674	Discontinued
0.7808	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3817	Phase 2
0.7785	Intermediate Similarity	NPD7447	Phase 1
0.7785	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7472	Approved
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7746	Intermediate Similarity	NPD3620	Phase 2
0.7746	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD2684	Approved
0.7727	Intermediate Similarity	NPD6671	Approved
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD6099	Approved
0.7721	Intermediate Similarity	NPD1091	Approved
0.7721	Intermediate Similarity	NPD422	Phase 1
0.7718	Intermediate Similarity	NPD7212	Phase 2
0.7718	Intermediate Similarity	NPD7213	Phase 3
0.7698	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5124	Phase 1
0.7681	Intermediate Similarity	NPD8651	Approved
0.7671	Intermediate Similarity	NPD3540	Phase 1
0.7671	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD37	Approved
0.7655	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4675	Approved
0.7647	Intermediate Similarity	NPD4678	Approved
0.764	Intermediate Similarity	NPD7228	Approved
0.7634	Intermediate Similarity	NPD7843	Approved
0.7628	Intermediate Similarity	NPD4967	Phase 2
0.7628	Intermediate Similarity	NPD4965	Approved
0.7628	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD1549	Phase 2
0.7613	Intermediate Similarity	NPD1465	Phase 2
0.7609	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6797	Phase 2
0.7603	Intermediate Similarity	NPD3539	Phase 1
0.7595	Intermediate Similarity	NPD5494	Approved
0.7594	Intermediate Similarity	NPD7157	Approved
0.7593	Intermediate Similarity	NPD5844	Phase 1
0.7586	Intermediate Similarity	NPD4538	Approved
0.7586	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4536	Approved
0.7584	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7075	Discontinued
0.7571	Intermediate Similarity	NPD6584	Phase 3
0.7568	Intermediate Similarity	NPD1652	Phase 2
0.7568	Intermediate Similarity	NPD5177	Phase 3
0.7561	Intermediate Similarity	NPD7251	Discontinued
0.7551	Intermediate Similarity	NPD7266	Discontinued
0.7551	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.753	Intermediate Similarity	NPD8054	Approved
0.753	Intermediate Similarity	NPD8053	Approved
0.7519	Intermediate Similarity	NPD290	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3892	Phase 2
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7549	Discontinued
0.7515	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7468	Intermediate Similarity	NPD4005	Discontinued
0.7468	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3705	Approved
0.7452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6355	Discontinued
0.7445	Intermediate Similarity	NPD6516	Phase 2
0.7445	Intermediate Similarity	NPD5846	Approved
0.7434	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7124	Phase 2
0.7415	Intermediate Similarity	NPD1510	Phase 2
0.7415	Intermediate Similarity	NPD5960	Phase 3
0.7415	Intermediate Similarity	NPD5588	Approved
0.7413	Intermediate Similarity	NPD7095	Approved
0.7405	Intermediate Similarity	NPD4750	Phase 3
0.7402	Intermediate Similarity	NPD846	Approved
0.7402	Intermediate Similarity	NPD940	Approved
0.74	Intermediate Similarity	NPD7466	Approved
0.74	Intermediate Similarity	NPD3750	Approved
0.74	Intermediate Similarity	NPD6331	Phase 2
0.7391	Intermediate Similarity	NPD6232	Discontinued
0.7389	Intermediate Similarity	NPD7819	Suspended
0.7386	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4357	Discontinued
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6799	Approved
0.7365	Intermediate Similarity	NPD2796	Approved
0.7362	Intermediate Similarity	NPD7473	Discontinued
0.7357	Intermediate Similarity	NPD6583	Phase 3
0.7357	Intermediate Similarity	NPD6582	Phase 2
0.7355	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3060	Approved
0.7329	Intermediate Similarity	NPD5735	Approved
0.7323	Intermediate Similarity	NPD1242	Phase 1
0.732	Intermediate Similarity	NPD4123	Phase 3
0.732	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5763	Approved
0.7315	Intermediate Similarity	NPD5762	Approved
0.7308	Intermediate Similarity	NPD968	Approved
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7301	Intermediate Similarity	NPD2489	Approved
0.7301	Intermediate Similarity	NPD27	Approved
0.7285	Intermediate Similarity	NPD4110	Phase 3
0.7285	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7411	Suspended
0.726	Intermediate Similarity	NPD1240	Approved
0.7254	Intermediate Similarity	NPD2797	Approved
0.7246	Intermediate Similarity	NPD1357	Approved
0.7246	Intermediate Similarity	NPD6559	Discontinued
0.7239	Intermediate Similarity	NPD2969	Approved
0.7239	Intermediate Similarity	NPD2970	Approved
0.7239	Intermediate Similarity	NPD5535	Approved
0.7237	Intermediate Similarity	NPD2677	Approved
0.723	Intermediate Similarity	NPD6111	Discontinued
0.7226	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4237	Approved
0.7219	Intermediate Similarity	NPD4162	Approved
0.7219	Intermediate Similarity	NPD4236	Phase 3
0.7215	Intermediate Similarity	NPD6801	Discontinued
0.7211	Intermediate Similarity	NPD230	Phase 1
0.7211	Intermediate Similarity	NPD4340	Discontinued
0.7208	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1375	Discontinued
0.7197	Intermediate Similarity	NPD6599	Discontinued
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7188	Intermediate Similarity	NPD7768	Phase 2
0.7181	Intermediate Similarity	NPD7033	Discontinued
0.7178	Intermediate Similarity	NPD3051	Approved
0.7171	Intermediate Similarity	NPD4628	Phase 3
0.7169	Intermediate Similarity	NPD8156	Discontinued
0.7169	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD1607	Approved
0.716	Intermediate Similarity	NPD7313	Approved
0.716	Intermediate Similarity	NPD4578	Approved
0.716	Intermediate Similarity	NPD7311	Approved
0.716	Intermediate Similarity	NPD7312	Approved
0.716	Intermediate Similarity	NPD7310	Approved
0.716	Intermediate Similarity	NPD4577	Approved
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7152	Intermediate Similarity	NPD6072	Discontinued
0.7143	Intermediate Similarity	NPD1774	Approved
0.7143	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD7240	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