NPASS Compound

Structure

NPC204215 OpenBabel07101718322D 30 32 0 0 1 0 0 0 0 0999 V2000 1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4662 1.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8283 -2.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2350 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0649 0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2460 -1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6527 -0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4716 1.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8337 -2.1521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6472 -0.3250 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 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 2 1 1 0 0 0 13 22 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 21 14 1 6 0 0 0 21 30 1 0 0 0 0 22 15 1 6 0 0 0 22 30 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.2
Volume:	426.408
LogP:	3.941
LogD:	3.547
LogS:	-4.852
# Rotatable Bonds:	7
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	3.51
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.724
MDCK Permeability:	3.8478228816529736e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.483

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	74.6060791015625%
Volume Distribution (VD):	0.596
Pgp-substrate:	22.35614585876465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.526
CYP2C9-substrate:	0.786
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	9.189
Half-life (T1/2):	0.513

ADMET: Toxicity

hERG Blockers:	0.24
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.901
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.053
Respiratory Toxicity:	0.146

Download Data

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

Natural Product: NPC204215

Natural Product ID:	NPC204215
*Common Name:**	(-)-(7S,8S,7'r,8'r)-4-Hydroxy-3,5,3',4',5'-Pentamethoxy-7,7'-Epoxylignan
IUPAC Name:	4-[(2S,3S,4R,5R)-3,4-dimethyl-5-(3,4,5-trimethoxyphenyl)oxolan-2-yl]-2,6-dimethoxyphenol
Synonyms:
Standard InCHIKey:	BJMZZPKIBSAQBA-AHIIRKPMSA-N
Standard InCHI:	InChI=1S/C23H30O7/c1-12-13(2)22(15-10-18(27-5)23(29-7)19(11-15)28-6)30-21(12)14-8-16(25-3)20(24)17(9-14)26-4/h8-13,21-22,24H,1-7H3/t12-,13+,21-,22+/m0/s1
SMILES:	C[C@H]1[C@@H](C)[C@H](c2cc(c(c(c2)OC)OC)OC)O[C@@H]1c1cc(c(c(c1)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105541
PubChem CID:	76335614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/EC50	=	2.2	n.a.	PMID[462914]
NPT27	Others	Unspecified		CC50	=	65800.0	nM	PMID[462914]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	29500.0	nM	PMID[462914]

☑ 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 NPC204215 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	393
0.1-0.2	1320
0.2-0.3	3760
0.3-0.4	10304
0.4-0.5	8694
0.5-0.6	4409
0.6-0.7	8096
0.7-0.8	4100
0.8-0.85	864
0.85-0.9	584
0.9-0.95	142
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC175067
0.9921	High Similarity	NPC158331
0.9843	High Similarity	NPC287745
0.9843	High Similarity	NPC326095
0.9843	High Similarity	NPC244983
0.9766	High Similarity	NPC126409
0.9766	High Similarity	NPC141765
0.9766	High Similarity	NPC99572
0.9766	High Similarity	NPC165155
0.9766	High Similarity	NPC34103
0.9766	High Similarity	NPC24490
0.9606	High Similarity	NPC474017
0.9528	High Similarity	NPC242807
0.9528	High Similarity	NPC153739
0.9528	High Similarity	NPC241522
0.9528	High Similarity	NPC64201
0.9528	High Similarity	NPC92164
0.9528	High Similarity	NPC257582
0.9528	High Similarity	NPC145305
0.9528	High Similarity	NPC42300
0.9528	High Similarity	NPC174495
0.9528	High Similarity	NPC77040
0.9528	High Similarity	NPC187998
0.9524	High Similarity	NPC128208
0.9524	High Similarity	NPC45774
0.9524	High Similarity	NPC129570
0.9524	High Similarity	NPC21867
0.9524	High Similarity	NPC184733
0.9524	High Similarity	NPC282703
0.9524	High Similarity	NPC11258
0.952	High Similarity	NPC76451
0.947	High Similarity	NPC160283
0.947	High Similarity	NPC254759
0.947	High Similarity	NPC177868
0.947	High Similarity	NPC184797
0.947	High Similarity	NPC309124
0.9466	High Similarity	NPC474039
0.9453	High Similarity	NPC27843
0.9453	High Similarity	NPC115207
0.9453	High Similarity	NPC158079
0.9453	High Similarity	NPC277804
0.9453	High Similarity	NPC7171
0.9453	High Similarity	NPC161557
0.9453	High Similarity	NPC40432
0.9453	High Similarity	NPC228346
0.9449	High Similarity	NPC170844
0.9449	High Similarity	NPC475875
0.9449	High Similarity	NPC476968
0.9444	High Similarity	NPC127587
0.9398	High Similarity	NPC247291
0.9398	High Similarity	NPC87725
0.9398	High Similarity	NPC311530
0.9398	High Similarity	NPC263261
0.9394	High Similarity	NPC473739
0.9394	High Similarity	NPC236306
0.9394	High Similarity	NPC292882
0.9394	High Similarity	NPC232164
0.938	High Similarity	NPC201587
0.938	High Similarity	NPC181049
0.938	High Similarity	NPC207400
0.938	High Similarity	NPC253105
0.937	High Similarity	NPC206615
0.937	High Similarity	NPC470213
0.937	High Similarity	NPC98631
0.937	High Similarity	NPC186843
0.937	High Similarity	NPC470084
0.9365	High Similarity	NPC9891
0.9365	High Similarity	NPC285725
0.9365	High Similarity	NPC88297
0.9365	High Similarity	NPC186845
0.9365	High Similarity	NPC50683
0.9365	High Similarity	NPC112571
0.9328	High Similarity	NPC107161
0.9302	High Similarity	NPC470095
0.9302	High Similarity	NPC472597
0.9302	High Similarity	NPC309787
0.9302	High Similarity	NPC470096
0.9291	High Similarity	NPC473092
0.9291	High Similarity	NPC118533
0.9291	High Similarity	NPC165045
0.9291	High Similarity	NPC473093
0.9291	High Similarity	NPC8050
0.9286	High Similarity	NPC208950
0.9286	High Similarity	NPC472093
0.9286	High Similarity	NPC203133
0.9286	High Similarity	NPC193544
0.9286	High Similarity	NPC475169
0.9286	High Similarity	NPC17943
0.9286	High Similarity	NPC233410
0.9286	High Similarity	NPC298757
0.9286	High Similarity	NPC116907
0.9286	High Similarity	NPC221077
0.9286	High Similarity	NPC57490
0.9286	High Similarity	NPC251855
0.9286	High Similarity	NPC117214
0.9259	High Similarity	NPC102044
0.9259	High Similarity	NPC298317
0.9259	High Similarity	NPC185071
0.9259	High Similarity	NPC12728
0.9259	High Similarity	NPC255566
0.9259	High Similarity	NPC47633
0.9259	High Similarity	NPC477616
0.9259	High Similarity	NPC85264
0.9248	High Similarity	NPC471183
0.9242	High Similarity	NPC133025
0.9242	High Similarity	NPC248727
0.9242	High Similarity	NPC270456
0.9242	High Similarity	NPC265433
0.9242	High Similarity	NPC162659
0.9237	High Similarity	NPC67247
0.9231	High Similarity	NPC35932
0.9231	High Similarity	NPC160991
0.9231	High Similarity	NPC470752
0.9231	High Similarity	NPC6451
0.9231	High Similarity	NPC4940
0.9231	High Similarity	NPC7903
0.9231	High Similarity	NPC16208
0.9231	High Similarity	NPC184447
0.9225	High Similarity	NPC472338
0.9219	High Similarity	NPC222127
0.9219	High Similarity	NPC82862
0.9219	High Similarity	NPC328682
0.9219	High Similarity	NPC281864
0.9219	High Similarity	NPC54321
0.9213	High Similarity	NPC206882
0.9191	High Similarity	NPC473046
0.9191	High Similarity	NPC63879
0.9191	High Similarity	NPC118385
0.9191	High Similarity	NPC472712
0.9191	High Similarity	NPC472713
0.9191	High Similarity	NPC470097
0.9191	High Similarity	NPC93323
0.9191	High Similarity	NPC114119
0.9191	High Similarity	NPC12641
0.9191	High Similarity	NPC187774
0.9191	High Similarity	NPC471415
0.9191	High Similarity	NPC45257
0.9191	High Similarity	NPC280092
0.9185	High Similarity	NPC41782
0.9179	High Similarity	NPC27495
0.9179	High Similarity	NPC266197
0.9179	High Similarity	NPC291101
0.9173	High Similarity	NPC156948
0.9173	High Similarity	NPC86605
0.9173	High Similarity	NPC46277
0.9173	High Similarity	NPC477938
0.9173	High Similarity	NPC301765
0.9173	High Similarity	NPC3072
0.9167	High Similarity	NPC94750
0.9167	High Similarity	NPC121812
0.9167	High Similarity	NPC134968
0.9167	High Similarity	NPC112246
0.9167	High Similarity	NPC256262
0.9167	High Similarity	NPC260898
0.9167	High Similarity	NPC234333
0.9167	High Similarity	NPC112939
0.9167	High Similarity	NPC474206
0.9167	High Similarity	NPC47398
0.9167	High Similarity	NPC470356
0.916	High Similarity	NPC475840
0.9154	High Similarity	NPC474356
0.9154	High Similarity	NPC12275
0.9154	High Similarity	NPC45715
0.9154	High Similarity	NPC232275
0.9147	High Similarity	NPC212015
0.9147	High Similarity	NPC3439
0.9147	High Similarity	NPC226788
0.9147	High Similarity	NPC218856
0.9147	High Similarity	NPC210623
0.9147	High Similarity	NPC273295
0.9147	High Similarity	NPC190629
0.9147	High Similarity	NPC222004
0.9147	High Similarity	NPC202582
0.9147	High Similarity	NPC285339
0.9147	High Similarity	NPC470258
0.9141	High Similarity	NPC236791
0.9141	High Similarity	NPC293054
0.9141	High Similarity	NPC210355
0.9141	High Similarity	NPC82679
0.9141	High Similarity	NPC246620
0.9141	High Similarity	NPC324112
0.9141	High Similarity	NPC282000
0.9141	High Similarity	NPC169474
0.9141	High Similarity	NPC124452
0.9141	High Similarity	NPC159968
0.9141	High Similarity	NPC74817
0.9141	High Similarity	NPC5428
0.9134	High Similarity	NPC148627
0.9127	High Similarity	NPC228922
0.9127	High Similarity	NPC165375
0.9127	High Similarity	NPC220598
0.9127	High Similarity	NPC233526
0.9127	High Similarity	NPC31344
0.9127	High Similarity	NPC317769
0.9127	High Similarity	NPC282496
0.9127	High Similarity	NPC197757
0.9127	High Similarity	NPC136319
0.9124	High Similarity	NPC477702
0.9111	High Similarity	NPC471389
0.9104	High Similarity	NPC127218

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 NPC204215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	792
0.2-0.3	1841
0.3-0.4	2781
0.4-0.5	1705
0.5-0.6	999
0.6-0.7	596
0.7-0.8	109
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9449	High Similarity	NPD3027	Phase 3
0.8797	High Similarity	NPD1612	Clinical (unspecified phase)
0.8797	High Similarity	NPD1613	Approved
0.8702	High Similarity	NPD1530	Clinical (unspecified phase)
0.8636	High Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8254	Intermediate Similarity	NPD5283	Phase 1
0.8222	Intermediate Similarity	NPD4908	Phase 1
0.8121	Intermediate Similarity	NPD37	Approved
0.812	Intermediate Similarity	NPD2983	Phase 2
0.812	Intermediate Similarity	NPD2982	Phase 2
0.8116	Intermediate Similarity	NPD3620	Phase 2
0.8116	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1610	Phase 2
0.8106	Intermediate Similarity	NPD3705	Approved
0.8102	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD228	Approved
0.8079	Intermediate Similarity	NPD4965	Approved
0.8079	Intermediate Similarity	NPD4966	Approved
0.8079	Intermediate Similarity	NPD4967	Phase 2
0.8045	Intermediate Similarity	NPD2981	Phase 2
0.8015	Intermediate Similarity	NPD2861	Phase 2
0.8015	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD1934	Approved
0.7962	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD3022	Approved
0.7937	Intermediate Similarity	NPD3021	Approved
0.7852	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4749	Approved
0.7843	Intermediate Similarity	NPD3882	Suspended
0.7829	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1548	Phase 1
0.7727	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2801	Approved
0.7682	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4625	Phase 3
0.7643	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD1653	Approved
0.7612	Intermediate Similarity	NPD1357	Approved
0.761	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6166	Phase 2
0.761	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1558	Phase 1
0.7606	Intermediate Similarity	NPD4060	Phase 1
0.7566	Intermediate Similarity	NPD4005	Discontinued
0.7551	Intermediate Similarity	NPD4237	Approved
0.7551	Intermediate Similarity	NPD4236	Phase 3
0.7551	Intermediate Similarity	NPD6674	Discontinued
0.7547	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7266	Discontinued
0.7517	Intermediate Similarity	NPD7124	Phase 2
0.7516	Intermediate Similarity	NPD4675	Approved
0.7516	Intermediate Similarity	NPD4678	Approved
0.7468	Intermediate Similarity	NPD5494	Approved
0.7467	Intermediate Similarity	NPD1511	Approved
0.7467	Intermediate Similarity	NPD4357	Discontinued
0.7467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6111	Discontinued
0.7444	Intermediate Similarity	NPD7157	Approved
0.7442	Intermediate Similarity	NPD2684	Approved
0.7439	Intermediate Similarity	NPD7240	Approved
0.7432	Intermediate Similarity	NPD3060	Approved
0.7432	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD230	Phase 1
0.7423	Intermediate Similarity	NPD7074	Phase 3
0.7415	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3540	Phase 1
0.741	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5588	Approved
0.7385	Intermediate Similarity	NPD4750	Phase 3
0.7383	Intermediate Similarity	NPD6331	Phase 2
0.7383	Intermediate Similarity	NPD4110	Phase 3
0.7383	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2977	Approved
0.7372	Intermediate Similarity	NPD2978	Approved
0.7368	Intermediate Similarity	NPD1512	Approved
0.7362	Intermediate Similarity	NPD7054	Approved
0.7361	Intermediate Similarity	NPD2238	Phase 2
0.7348	Intermediate Similarity	NPD7843	Approved
0.7347	Intermediate Similarity	NPD3539	Phase 1
0.7343	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5536	Phase 2
0.7333	Intermediate Similarity	NPD2219	Phase 1
0.7329	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4536	Approved
0.7329	Intermediate Similarity	NPD4538	Approved
0.7325	Intermediate Similarity	NPD3817	Phase 2
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1091	Approved
0.7317	Intermediate Similarity	NPD7472	Approved
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.731	Intermediate Similarity	NPD6355	Discontinued
0.731	Intermediate Similarity	NPD3657	Discovery
0.731	Intermediate Similarity	NPD5735	Approved
0.7302	Intermediate Similarity	NPD1242	Phase 1
0.7297	Intermediate Similarity	NPD1375	Discontinued
0.729	Intermediate Similarity	NPD4380	Phase 2
0.7285	Intermediate Similarity	NPD5058	Phase 3
0.7267	Intermediate Similarity	NPD3892	Phase 2
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7262	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1465	Phase 2
0.7256	Intermediate Similarity	NPD5844	Phase 1
0.7239	Intermediate Similarity	NPD7473	Discontinued
0.7234	Intermediate Similarity	NPD3094	Phase 2
0.723	Intermediate Similarity	NPD6100	Approved
0.723	Intermediate Similarity	NPD6099	Approved
0.723	Intermediate Similarity	NPD2161	Phase 2
0.7222	Intermediate Similarity	NPD5111	Phase 2
0.7222	Intermediate Similarity	NPD5109	Approved
0.7222	Intermediate Similarity	NPD5110	Phase 2
0.7222	Intermediate Similarity	NPD3020	Approved
0.7219	Intermediate Similarity	NPD6190	Approved
0.7194	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD4123	Phase 3
0.7185	Intermediate Similarity	NPD6671	Approved
0.7183	Intermediate Similarity	NPD6584	Phase 3
0.7181	Intermediate Similarity	NPD5763	Approved
0.7181	Intermediate Similarity	NPD5762	Approved
0.7172	Intermediate Similarity	NPD2674	Phase 3
0.7169	Intermediate Similarity	NPD6797	Phase 2
0.7169	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8651	Approved
0.7163	Intermediate Similarity	NPD6696	Suspended
0.7162	Intermediate Similarity	NPD5960	Phase 3
0.7154	Intermediate Similarity	NPD968	Approved
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6653	Approved
0.7133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7124	Intermediate Similarity	NPD7213	Phase 3
0.7124	Intermediate Similarity	NPD7212	Phase 2
0.7109	Intermediate Similarity	NPD940	Approved
0.7109	Intermediate Similarity	NPD846	Approved
0.7107	Intermediate Similarity	NPD2560	Approved
0.7107	Intermediate Similarity	NPD2563	Approved
0.7105	Intermediate Similarity	NPD2677	Approved
0.7103	Intermediate Similarity	NPD3144	Approved
0.7103	Intermediate Similarity	NPD3145	Approved
0.7102	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD290	Approved
0.7092	Intermediate Similarity	NPD5327	Phase 3
0.7086	Intermediate Similarity	NPD1652	Phase 2
0.7086	Intermediate Similarity	NPD4162	Approved
0.7083	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7808	Phase 3
0.7083	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7549	Discontinued
0.7078	Intermediate Similarity	NPD2534	Approved
0.7078	Intermediate Similarity	NPD2533	Approved
0.7078	Intermediate Similarity	NPD7447	Phase 1
0.7078	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2532	Approved
0.7075	Intermediate Similarity	NPD5124	Phase 1
0.7075	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD27	Approved
0.7073	Intermediate Similarity	NPD2489	Approved
0.7071	Intermediate Similarity	NPD3092	Approved
0.7067	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.705	Intermediate Similarity	NPD5125	Phase 3
0.705	Intermediate Similarity	NPD5846	Approved
0.705	Intermediate Similarity	NPD5126	Approved
0.705	Intermediate Similarity	NPD6516	Phase 2
0.7047	Intermediate Similarity	NPD1510	Phase 2
0.7047	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5772	Approved
0.7044	Intermediate Similarity	NPD5773	Approved
0.7041	Intermediate Similarity	NPD7313	Approved
0.7041	Intermediate Similarity	NPD7312	Approved
0.7041	Intermediate Similarity	NPD4578	Approved
0.7041	Intermediate Similarity	NPD7311	Approved
0.7041	Intermediate Similarity	NPD4577	Approved
0.7041	Intermediate Similarity	NPD7310	Approved
0.7039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7466	Approved
0.7032	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD52	Approved
0.7032	Intermediate Similarity	NPD7526	Approved
0.7024	Intermediate Similarity	NPD7685	Pre-registration
0.7024	Intermediate Similarity	NPD6559	Discontinued
0.7021	Intermediate Similarity	NPD2232	Approved
0.7021	Intermediate Similarity	NPD1608	Approved
0.7021	Intermediate Similarity	NPD2235	Phase 2
0.7021	Intermediate Similarity	NPD2233	Approved
0.7021	Intermediate Similarity	NPD2230	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