NPASS Compound

Structure

NPC77861 OpenBabel07101718202D 38 41 0 0 1 0 0 0 0 0999 V2000 0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -0.4067 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 -3.5116 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.4067 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 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 -1.9067 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 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 0.0933 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 -1.7796 1.0933 0.0000 C 0 0 0 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 -0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 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 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -1.4067 0.0000 C 0 0 0 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 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -0.4067 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 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7078 -1.9067 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 -4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 0.0933 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 -2.6456 2.5933 0.0000 O 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 10 2 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 20 2 0 0 0 0 14 26 1 0 0 0 0 15 21 2 0 0 0 0 15 27 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 2 1 1 0 0 0 17 30 1 0 0 0 0 18 3 1 1 0 0 0 18 28 1 0 0 0 0 18 37 1 0 0 0 0 19 28 1 0 0 0 0 22 25 2 0 0 0 0 22 31 1 0 0 0 0 23 26 2 0 0 0 0 23 32 1 0 0 0 0 24 27 2 0 0 0 0 24 37 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 33 1 6 0 0 0 29 20 1 6 0 0 0 29 38 1 0 0 0 0 30 21 1 6 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.24
Volume:	539.804
LogP:	5.091
LogD:	4.108
LogS:	-4.775
# Rotatable Bonds:	9
TPSA:	106.84
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	4.032
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
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:	-5.327
MDCK Permeability:	1.5684348909417167e-05
Pgp-inhibitor:	0.808
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.0572738647461%
Volume Distribution (VD):	0.516
Pgp-substrate:	5.9036784172058105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.694
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.386
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	4.758
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.222
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.083
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC77861

Natural Product ID:	NPC77861
*Common Name:**	(-)-(7''r,8''r)-Saucerneol J
IUPAC Name:	4-[(2S,3R,4R,5R)-5-[4-[(1R,2R)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	GIBPGXUIRFWSNY-ZCZCRYHXSA-N
Standard InCHI:	InChI=1S/C30H36O8/c1-16-17(2)30(38-29(16)20-8-11-23(32)26(14-20)35-5)21-9-12-24(27(15-21)36-6)37-18(3)28(33)19-7-10-22(31)25(13-19)34-4/h7-18,28-33H,1-6H3/t16-,17-,18-,28+,29+,30-/m1/s1
SMILES:	C[C@@H]1[C@@H](C)[C@H](c2ccc(c(c2)OC)O[C@H](C)[C@@H](c2ccc(c(c2)OC)O)O)O[C@@H]1c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105543
PubChem CID:	73890954
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	=	3.3	n.a.	PMID[559444]
NPT27	Others	Unspecified		CC50	=	23200.0	nM	PMID[559444]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	6950.0	nM	PMID[559444]

☑ 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 NPC77861 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	402
0.1-0.2	1299
0.2-0.3	3418
0.3-0.4	9677
0.4-0.5	9448
0.5-0.6	4669
0.6-0.7	8738
0.7-0.8	3744
0.8-0.85	804
0.85-0.9	390
0.9-0.95	104
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC93783
0.9699	High Similarity	NPC470372
0.9549	High Similarity	NPC260842
0.9485	High Similarity	NPC114119
0.9485	High Similarity	NPC471415
0.9485	High Similarity	NPC470097
0.9478	High Similarity	NPC266197
0.9478	High Similarity	NPC291101
0.9478	High Similarity	NPC55793
0.9385	High Similarity	NPC92164
0.9385	High Similarity	NPC187998
0.9385	High Similarity	NPC64201
0.9385	High Similarity	NPC153739
0.9385	High Similarity	NPC257582
0.9385	High Similarity	NPC77040
0.9385	High Similarity	NPC242807
0.9385	High Similarity	NPC241522
0.9385	High Similarity	NPC42300
0.9385	High Similarity	NPC174495
0.9385	High Similarity	NPC145305
0.938	High Similarity	NPC128208
0.938	High Similarity	NPC11258
0.938	High Similarity	NPC282703
0.938	High Similarity	NPC45774
0.938	High Similarity	NPC184733
0.938	High Similarity	NPC21867
0.938	High Similarity	NPC129570
0.9348	High Similarity	NPC317053
0.9348	High Similarity	NPC324492
0.9348	High Similarity	NPC260397
0.9338	High Similarity	NPC476356
0.9338	High Similarity	NPC302506
0.9313	High Similarity	NPC277804
0.9308	High Similarity	NPC475875
0.9281	High Similarity	NPC320970
0.9281	High Similarity	NPC328567
0.9281	High Similarity	NPC320671
0.9281	High Similarity	NPC327412
0.927	High Similarity	NPC185307
0.927	High Similarity	NPC470950
0.9259	High Similarity	NPC22517
0.9254	High Similarity	NPC477939
0.9254	High Similarity	NPC177160
0.9254	High Similarity	NPC209985
0.9254	High Similarity	NPC10737
0.9254	High Similarity	NPC156502
0.9254	High Similarity	NPC54743
0.9254	High Similarity	NPC263367
0.9254	High Similarity	NPC29799
0.9248	High Similarity	NPC193026
0.9248	High Similarity	NPC187616
0.9248	High Similarity	NPC471942
0.9248	High Similarity	NPC49603
0.9231	High Similarity	NPC470084
0.9225	High Similarity	NPC58607
0.9225	High Similarity	NPC191037
0.9225	High Similarity	NPC178284
0.9214	High Similarity	NPC304048
0.9214	High Similarity	NPC226153
0.9203	High Similarity	NPC129417
0.9203	High Similarity	NPC470235
0.9203	High Similarity	NPC283995
0.9203	High Similarity	NPC179521
0.9167	High Similarity	NPC161557
0.9167	High Similarity	NPC228346
0.9167	High Similarity	NPC158079
0.9167	High Similarity	NPC115207
0.9167	High Similarity	NPC7171
0.9167	High Similarity	NPC27843
0.9167	High Similarity	NPC40432
0.916	High Similarity	NPC86030
0.916	High Similarity	NPC5851
0.9154	High Similarity	NPC163332
0.9154	High Similarity	NPC118787
0.9154	High Similarity	NPC41706
0.9154	High Similarity	NPC165045
0.9154	High Similarity	NPC147821
0.9154	High Similarity	NPC292056
0.9154	High Similarity	NPC319625
0.9154	High Similarity	NPC118533
0.9154	High Similarity	NPC183181
0.9154	High Similarity	NPC111247
0.9149	High Similarity	NPC473266
0.9149	High Similarity	NPC470098
0.9149	High Similarity	NPC470826
0.9147	High Similarity	NPC148627
0.9147	High Similarity	NPC194519
0.9137	High Similarity	NPC38041
0.9137	High Similarity	NPC181615
0.9137	High Similarity	NPC22150
0.9137	High Similarity	NPC279298
0.913	High Similarity	NPC46092
0.9124	High Similarity	NPC472711
0.9104	High Similarity	NPC287745
0.9104	High Similarity	NPC478085
0.9104	High Similarity	NPC326095
0.9104	High Similarity	NPC244983
0.9098	High Similarity	NPC181049
0.9098	High Similarity	NPC4940
0.9098	High Similarity	NPC207400
0.9084	High Similarity	NPC72529
0.9084	High Similarity	NPC474178
0.9084	High Similarity	NPC252307
0.9084	High Similarity	NPC245826
0.9077	High Similarity	NPC206882
0.9071	High Similarity	NPC112861
0.9071	High Similarity	NPC93610
0.9071	High Similarity	NPC241846
0.907	High Similarity	NPC109822
0.907	High Similarity	NPC94276
0.9058	High Similarity	NPC67467
0.9051	High Similarity	NPC309124
0.9051	High Similarity	NPC184797
0.903	High Similarity	NPC26394
0.903	High Similarity	NPC158331
0.9021	High Similarity	NPC324517
0.9021	High Similarity	NPC329343
0.9021	High Similarity	NPC321972
0.9008	High Similarity	NPC5428
0.9007	High Similarity	NPC275284
0.9007	High Similarity	NPC15956
0.9007	High Similarity	NPC224674
0.9007	High Similarity	NPC193473
0.9007	High Similarity	NPC213074
0.9007	High Similarity	NPC99183
0.9007	High Similarity	NPC31325
0.9007	High Similarity	NPC39657
0.9007	High Similarity	NPC114505
0.9	High Similarity	NPC18979
0.8993	High Similarity	NPC477898
0.8992	High Similarity	NPC317769
0.8992	High Similarity	NPC31344
0.8992	High Similarity	NPC471693
0.8986	High Similarity	NPC471414
0.8986	High Similarity	NPC87725
0.8986	High Similarity	NPC263261
0.8986	High Similarity	NPC178054
0.8986	High Similarity	NPC311530
0.8978	High Similarity	NPC236306
0.8978	High Similarity	NPC473739
0.8978	High Similarity	NPC232164
0.8971	High Similarity	NPC471988
0.8963	High Similarity	NPC170694
0.8963	High Similarity	NPC67247
0.8955	High Similarity	NPC160991
0.8955	High Similarity	NPC7903
0.8955	High Similarity	NPC175067
0.8955	High Similarity	NPC471505
0.8955	High Similarity	NPC230219
0.8955	High Similarity	NPC106739
0.8955	High Similarity	NPC184447
0.8955	High Similarity	NPC470752
0.8955	High Similarity	NPC204215
0.8955	High Similarity	NPC35932
0.8955	High Similarity	NPC16208
0.8929	High Similarity	NPC84181
0.8923	High Similarity	NPC114901
0.8923	High Similarity	NPC48990
0.8923	High Similarity	NPC293701
0.8921	High Similarity	NPC253878
0.8921	High Similarity	NPC107161
0.8921	High Similarity	NPC246947
0.8921	High Similarity	NPC131971
0.8915	High Similarity	NPC71090
0.8915	High Similarity	NPC85488
0.8913	High Similarity	NPC160283
0.8913	High Similarity	NPC254759
0.8905	High Similarity	NPC138738
0.8905	High Similarity	NPC470413
0.8905	High Similarity	NPC281780
0.8905	High Similarity	NPC474390
0.8897	High Similarity	NPC184938
0.8897	High Similarity	NPC24490
0.8897	High Similarity	NPC141765
0.8897	High Similarity	NPC470769
0.8897	High Similarity	NPC101624
0.8897	High Similarity	NPC34103
0.8897	High Similarity	NPC135777
0.8897	High Similarity	NPC126409
0.8897	High Similarity	NPC142547
0.8897	High Similarity	NPC165155
0.8897	High Similarity	NPC99572
0.8881	High Similarity	NPC55158
0.8881	High Similarity	NPC470095
0.8881	High Similarity	NPC309787
0.8881	High Similarity	NPC470096
0.8881	High Similarity	NPC469613
0.8881	High Similarity	NPC286235
0.8881	High Similarity	NPC30043
0.8881	High Similarity	NPC51328
0.8881	High Similarity	NPC474017
0.8881	High Similarity	NPC469625
0.8881	High Similarity	NPC472597
0.8865	High Similarity	NPC43508
0.8865	High Similarity	NPC476301
0.8857	High Similarity	NPC477616
0.8849	High Similarity	NPC247291
0.8849	High Similarity	NPC471389
0.8846	High Similarity	NPC473451
0.8846	High Similarity	NPC280704

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 NPC77861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	802
0.2-0.3	1654
0.3-0.4	2683
0.4-0.5	1864
0.5-0.6	1028
0.6-0.7	651
0.7-0.8	150
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8731	High Similarity	NPD3027	Phase 3
0.854	High Similarity	NPD1612	Clinical (unspecified phase)
0.854	High Similarity	NPD1613	Approved
0.8309	Intermediate Similarity	NPD2861	Phase 2
0.8273	Intermediate Similarity	NPD3620	Phase 2
0.8273	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5283	Phase 1
0.8116	Intermediate Similarity	NPD4908	Phase 1
0.8015	Intermediate Similarity	NPD7157	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD228	Approved
0.7958	Intermediate Similarity	NPD5735	Approved
0.7945	Intermediate Similarity	NPD6674	Discontinued
0.7923	Intermediate Similarity	NPD7843	Approved
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7868	Intermediate Similarity	NPD3705	Approved
0.7829	Intermediate Similarity	NPD3021	Approved
0.7829	Intermediate Similarity	NPD3022	Approved
0.7808	Intermediate Similarity	NPD7266	Discontinued
0.7792	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD7199	Phase 2
0.7764	Intermediate Similarity	NPD7228	Approved
0.7762	Intermediate Similarity	NPD1558	Phase 1
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7756	Intermediate Similarity	NPD4966	Approved
0.7756	Intermediate Similarity	NPD4965	Approved
0.7756	Intermediate Similarity	NPD4967	Phase 2
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2684	Approved
0.775	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6166	Phase 2
0.7737	Intermediate Similarity	NPD1610	Phase 2
0.7733	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD6516	Phase 2
0.7721	Intermediate Similarity	NPD5846	Approved
0.7714	Intermediate Similarity	NPD6584	Phase 3
0.7703	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD8651	Approved
0.7677	Intermediate Similarity	NPD1934	Approved
0.7676	Intermediate Similarity	NPD7095	Approved
0.7671	Intermediate Similarity	NPD5588	Approved
0.7651	Intermediate Similarity	NPD6331	Phase 2
0.7647	Intermediate Similarity	NPD1357	Approved
0.7643	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD5327	Phase 3
0.7603	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4538	Approved
0.7603	Intermediate Similarity	NPD4536	Approved
0.7586	Intermediate Similarity	NPD6355	Discontinued
0.7584	Intermediate Similarity	NPD4236	Phase 3
0.7584	Intermediate Similarity	NPD4237	Approved
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5762	Approved
0.7568	Intermediate Similarity	NPD5763	Approved
0.7562	Intermediate Similarity	NPD8127	Discontinued
0.755	Intermediate Similarity	NPD5058	Phase 3
0.7546	Intermediate Similarity	NPD3818	Discontinued
0.7533	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4110	Phase 3
0.7532	Intermediate Similarity	NPD1653	Approved
0.7517	Intermediate Similarity	NPD4140	Approved
0.7517	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6582	Phase 2
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD6583	Phase 3
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7481	Intermediate Similarity	NPD6671	Approved
0.7468	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3060	Approved
0.7455	Intermediate Similarity	NPD7074	Phase 3
0.745	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1375	Discontinued
0.7448	Intermediate Similarity	NPD6233	Phase 2
0.7445	Intermediate Similarity	NPD1548	Phase 1
0.7432	Intermediate Similarity	NPD5960	Phase 3
0.7429	Intermediate Similarity	NPD2981	Phase 2
0.7423	Intermediate Similarity	NPD2489	Approved
0.7423	Intermediate Similarity	NPD27	Approved
0.7421	Intermediate Similarity	NPD3882	Suspended
0.7417	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD6353	Approved
0.7415	Intermediate Similarity	NPD6653	Approved
0.7413	Intermediate Similarity	NPD3018	Phase 2
0.7407	Intermediate Similarity	NPD3051	Approved
0.7405	Intermediate Similarity	NPD5773	Approved
0.7405	Intermediate Similarity	NPD2977	Approved
0.7405	Intermediate Similarity	NPD2801	Approved
0.7405	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5772	Approved
0.7405	Intermediate Similarity	NPD2978	Approved
0.74	Intermediate Similarity	NPD7037	Approved
0.7396	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3094	Phase 2
0.7394	Intermediate Similarity	NPD7054	Approved
0.7383	Intermediate Similarity	NPD2161	Phase 2
0.7376	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4749	Approved
0.7372	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2677	Approved
0.7368	Intermediate Similarity	NPD6190	Approved
0.7365	Intermediate Similarity	NPD7097	Phase 1
0.7362	Intermediate Similarity	NPD2969	Approved
0.7362	Intermediate Similarity	NPD2970	Approved
0.7361	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3092	Approved
0.7357	Intermediate Similarity	NPD1091	Approved
0.7351	Intermediate Similarity	NPD4162	Approved
0.7349	Intermediate Similarity	NPD7472	Approved
0.7347	Intermediate Similarity	NPD3657	Discovery
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD968	Approved
0.7324	Intermediate Similarity	NPD6696	Suspended
0.7315	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7906	Approved
0.731	Intermediate Similarity	NPD4625	Phase 3
0.7305	Intermediate Similarity	NPD2231	Phase 2
0.7305	Intermediate Similarity	NPD2235	Phase 2
0.7303	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8455	Phase 2
0.729	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7526	Approved
0.729	Intermediate Similarity	NPD52	Approved
0.7289	Intermediate Similarity	NPD5844	Phase 1
0.7278	Intermediate Similarity	NPD7312	Approved
0.7278	Intermediate Similarity	NPD7311	Approved
0.7278	Intermediate Similarity	NPD7310	Approved
0.7278	Intermediate Similarity	NPD7313	Approved
0.7273	Intermediate Similarity	NPD290	Approved
0.7267	Intermediate Similarity	NPD7833	Phase 2
0.7267	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7831	Phase 2
0.7262	Intermediate Similarity	NPD7685	Pre-registration
0.7262	Intermediate Similarity	NPD7240	Approved
0.7259	Intermediate Similarity	NPD5535	Approved
0.7255	Intermediate Similarity	NPD5241	Discontinued
0.7251	Intermediate Similarity	NPD4663	Approved
0.725	Intermediate Similarity	NPD2560	Approved
0.725	Intermediate Similarity	NPD2563	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7237	Intermediate Similarity	NPD5177	Phase 3
0.7235	Intermediate Similarity	NPD7309	Approved
0.7226	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3686	Approved
0.7197	Intermediate Similarity	NPD3687	Approved
0.7195	Intermediate Similarity	NPD6071	Discontinued
0.7194	Intermediate Similarity	NPD3091	Approved
0.7183	Intermediate Similarity	NPD1608	Approved
0.7178	Intermediate Similarity	NPD5494	Approved
0.7176	Intermediate Similarity	NPD4578	Approved
0.7176	Intermediate Similarity	NPD4577	Approved
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7164	Intermediate Similarity	NPD5451	Approved
0.7162	Intermediate Similarity	NPD2238	Phase 2
0.7161	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7251	Discontinued
0.7154	Intermediate Similarity	NPD291	Approved
0.7143	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5111	Phase 2
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5110	Phase 2
0.7143	Intermediate Similarity	NPD5109	Approved
0.7143	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3020	Approved
0.7118	Intermediate Similarity	NPD7808	Phase 3
0.7115	Intermediate Similarity	NPD7447	Phase 1
0.7115	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4340	Discontinued
0.7107	Intermediate Similarity	NPD4675	Approved
0.7107	Intermediate Similarity	NPD4678	Approved
0.7103	Intermediate Similarity	NPD4624	Approved
0.7103	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6797	Phase 2
0.7097	Intermediate Similarity	NPD6815	Approved
0.7095	Intermediate Similarity	NPD2674	Phase 3
0.7095	Intermediate Similarity	NPD7265	Discontinued
0.7092	Intermediate Similarity	NPD5126	Approved
0.7092	Intermediate Similarity	NPD5125	Phase 3
0.7091	Intermediate Similarity	NPD6232	Discontinued
0.7089	Intermediate Similarity	NPD4210	Discontinued
0.7086	Intermediate Similarity	NPD7033	Discontinued
0.7078	Intermediate Similarity	NPD4535	Phase 3
0.7078	Intermediate Similarity	NPD7466	Approved
0.7078	Intermediate Similarity	NPD8166	Discontinued
0.7071	Intermediate Similarity	NPD6581	Approved
0.7071	Intermediate Similarity	NPD1182	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