NPASS Compound

Structure

CID210623 OpenBabel06191716002D 30 31 0 0 1 0 0 0 0 0999 V2000 9.5263 -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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 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 9 2 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 2 1 6 0 0 0 14 21 1 0 0 0 0 14 30 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 22 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 24 1 6 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.2
Volume:	432.328
LogP:	2.963
LogD:	3.062
LogS:	-3.819
# Rotatable Bonds:	10
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	3.221
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.667
MDCK Permeability:	3.699815715663135e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.243
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.31

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306
Plasma Protein Binding (PPB):	66.29166412353516%
Volume Distribution (VD):	0.631
Pgp-substrate:	28.434619903564453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.235
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.643
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	8.275
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.621
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.674
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC210623

Natural Product ID:	NPC210623
*Common Name:**	Polysyphorin
IUPAC Name:	(1S,2R)-2-[2,6-dimethoxy-4-[(E)-prop-1-enyl]phenoxy]-1-(3,4,5-trimethoxyphenyl)propan-1-ol
Synonyms:	Polysyphorin
Standard InCHIKey:	FLBWVIKFCMUTDS-IPHDZNCISA-N
Standard InCHI:	InChI=1S/C23H30O7/c1-8-9-15-10-17(25-3)23(18(11-15)26-4)30-14(2)21(24)16-12-19(27-5)22(29-7)20(13-16)28-6/h8-14,21,24H,1-7H3/b9-8+/t14-,21-/m1/s1
SMILES:	C/C=C/c1cc(OC)c(c(c1)OC)O[C@@H]([C@H](c1cc(OC)c(c(c1)OC)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460235
PubChem CID:	44559993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO863	Rhaphidophora decursiva	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421741]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO863	Rhaphidophora decursiva	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8666	Acorus tatarinowii	Species	Acoraceae	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
ED50	1
IC50	4
Others	2

Activity Type	# Activity
Cell Line	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[532269]
NPT2	Others	Unspecified		Selectivity Index	=	5.0	n.a.	PMID[532269]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.404	ug.mL-1	PMID[532269]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.368	ug.mL-1	PMID[532269]
NPT2	Others	Unspecified		Selectivity Index	=	6.0	n.a.	PMID[532269]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2720.0	nM	PMID[532270]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	IC50	=	9540.0	nM	PMID[532270]

☑ 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 NPC210623 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	368
0.1-0.2	1469
0.2-0.3	4692
0.3-0.4	12295
0.4-0.5	5777
0.5-0.6	4305
0.6-0.7	6988
0.7-0.8	4996
0.8-0.85	1022
0.85-0.9	551
0.9-0.95	186
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC190629
1.0	High Similarity	NPC218856
1.0	High Similarity	NPC470258
1.0	High Similarity	NPC222004
1.0	High Similarity	NPC3439
1.0	High Similarity	NPC285339
1.0	High Similarity	NPC202582
1.0	High Similarity	NPC226788
1.0	High Similarity	NPC273295
0.9839	High Similarity	NPC472597
0.9839	High Similarity	NPC469613
0.9839	High Similarity	NPC469625
0.9839	High Similarity	NPC30043
0.9836	High Similarity	NPC474119
0.976	High Similarity	NPC7903
0.976	High Similarity	NPC16208
0.976	High Similarity	NPC160991
0.976	High Similarity	NPC184447
0.976	High Similarity	NPC35932
0.9758	High Similarity	NPC472338
0.9758	High Similarity	NPC469612
0.9758	High Similarity	NPC469614
0.9606	High Similarity	NPC170694
0.9606	High Similarity	NPC310854
0.9603	High Similarity	NPC470752
0.959	High Similarity	NPC94276
0.959	High Similarity	NPC109822
0.9531	High Similarity	NPC472337
0.9531	High Similarity	NPC61946
0.9528	High Similarity	NPC263064
0.9528	High Similarity	NPC475840
0.9524	High Similarity	NPC470095
0.9524	High Similarity	NPC470096
0.9524	High Similarity	NPC309787
0.952	High Similarity	NPC170844
0.952	High Similarity	NPC476968
0.9516	High Similarity	NPC183181
0.9516	High Similarity	NPC118787
0.9516	High Similarity	NPC163332
0.9516	High Similarity	NPC111247
0.9516	High Similarity	NPC41706
0.9516	High Similarity	NPC210355
0.9516	High Similarity	NPC147821
0.9516	High Similarity	NPC319625
0.9516	High Similarity	NPC292056
0.9457	High Similarity	NPC16435
0.9457	High Similarity	NPC471719
0.9457	High Similarity	NPC306441
0.9457	High Similarity	NPC472336
0.9457	High Similarity	NPC172818
0.9457	High Similarity	NPC472334
0.9457	High Similarity	NPC25695
0.9449	High Similarity	NPC201587
0.9449	High Similarity	NPC253105
0.944	High Similarity	NPC98631
0.944	High Similarity	NPC186843
0.944	High Similarity	NPC206615
0.944	High Similarity	NPC470213
0.9435	High Similarity	NPC58607
0.9435	High Similarity	NPC178284
0.9435	High Similarity	NPC191037
0.9431	High Similarity	NPC293701
0.9431	High Similarity	NPC114901
0.9431	High Similarity	NPC48990
0.9426	High Similarity	NPC261661
0.9426	High Similarity	NPC71090
0.938	High Similarity	NPC47398
0.938	High Similarity	NPC121812
0.938	High Similarity	NPC234333
0.938	High Similarity	NPC94750
0.938	High Similarity	NPC112939
0.938	High Similarity	NPC260898
0.938	High Similarity	NPC474206
0.938	High Similarity	NPC112246
0.938	High Similarity	NPC470356
0.9375	High Similarity	NPC229442
0.9375	High Similarity	NPC168059
0.937	High Similarity	NPC474017
0.9365	High Similarity	NPC5851
0.9365	High Similarity	NPC86030
0.936	High Similarity	NPC242032
0.9355	High Similarity	NPC194519
0.9313	High Similarity	NPC22517
0.9308	High Similarity	NPC227503
0.9308	High Similarity	NPC474639
0.9308	High Similarity	NPC230734
0.9308	High Similarity	NPC302701
0.9308	High Similarity	NPC269091
0.9302	High Similarity	NPC287745
0.9302	High Similarity	NPC309744
0.9286	High Similarity	NPC72529
0.9274	High Similarity	NPC228972
0.9274	High Similarity	NPC122792
0.9262	High Similarity	NPC199023
0.9262	High Similarity	NPC472596
0.9242	High Similarity	NPC291101
0.9242	High Similarity	NPC266197
0.9242	High Similarity	NPC267291
0.9237	High Similarity	NPC103976
0.9237	High Similarity	NPC102904
0.9237	High Similarity	NPC176051
0.9237	High Similarity	NPC474282
0.9237	High Similarity	NPC107551
0.9237	High Similarity	NPC326797
0.9237	High Similarity	NPC474390
0.9237	High Similarity	NPC477938
0.9237	High Similarity	NPC211549
0.9231	High Similarity	NPC164787
0.9231	High Similarity	NPC151224
0.9225	High Similarity	NPC11060
0.9225	High Similarity	NPC158331
0.9213	High Similarity	NPC212015
0.9213	High Similarity	NPC469963
0.9213	High Similarity	NPC469951
0.9206	High Similarity	NPC470699
0.92	High Similarity	NPC17943
0.92	High Similarity	NPC203133
0.92	High Similarity	NPC472093
0.92	High Similarity	NPC57490
0.92	High Similarity	NPC298757
0.92	High Similarity	NPC475169
0.92	High Similarity	NPC193544
0.92	High Similarity	NPC221077
0.92	High Similarity	NPC251855
0.92	High Similarity	NPC208950
0.92	High Similarity	NPC117214
0.92	High Similarity	NPC116907
0.92	High Similarity	NPC233410
0.9194	High Similarity	NPC282496
0.9194	High Similarity	NPC165375
0.9194	High Similarity	NPC220598
0.9194	High Similarity	NPC233526
0.9173	High Similarity	NPC87725
0.9173	High Similarity	NPC471389
0.9173	High Similarity	NPC83375
0.9173	High Similarity	NPC224876
0.9173	High Similarity	NPC263261
0.9167	High Similarity	NPC471388
0.916	High Similarity	NPC270456
0.916	High Similarity	NPC248727
0.916	High Similarity	NPC162659
0.916	High Similarity	NPC265433
0.916	High Similarity	NPC470802
0.9154	High Similarity	NPC13745
0.9154	High Similarity	NPC326095
0.9154	High Similarity	NPC48863
0.9154	High Similarity	NPC244983
0.9154	High Similarity	NPC251981
0.9154	High Similarity	NPC317380
0.9147	High Similarity	NPC175067
0.9147	High Similarity	NPC61477
0.9147	High Similarity	NPC15658
0.9147	High Similarity	NPC185604
0.9147	High Similarity	NPC204215
0.9147	High Similarity	NPC78770
0.9147	High Similarity	NPC86655
0.9147	High Similarity	NPC127624
0.9147	High Similarity	NPC261619
0.9147	High Similarity	NPC202762
0.9147	High Similarity	NPC126029
0.9147	High Similarity	NPC219876
0.9141	High Similarity	NPC214860
0.9141	High Similarity	NPC91291
0.9134	High Similarity	NPC210674
0.9134	High Similarity	NPC252307
0.9134	High Similarity	NPC245826
0.9134	High Similarity	NPC31707
0.9134	High Similarity	NPC474178
0.9134	High Similarity	NPC470084
0.9127	High Similarity	NPC44748
0.9127	High Similarity	NPC18924
0.9127	High Similarity	NPC181361
0.9127	High Similarity	NPC78974
0.9127	High Similarity	NPC223136
0.9127	High Similarity	NPC103823
0.9127	High Similarity	NPC28730
0.9127	High Similarity	NPC214406
0.9113	High Similarity	NPC473411
0.9113	High Similarity	NPC71579
0.9113	High Similarity	NPC262253
0.9106	High Similarity	NPC166759
0.9104	High Similarity	NPC278469
0.9104	High Similarity	NPC189115
0.9104	High Similarity	NPC469559
0.9104	High Similarity	NPC193722
0.9098	High Similarity	NPC184797
0.9098	High Similarity	NPC160283
0.9098	High Similarity	NPC254759
0.9098	High Similarity	NPC135961
0.9098	High Similarity	NPC309124
0.9098	High Similarity	NPC22317
0.9091	High Similarity	NPC276490
0.9084	High Similarity	NPC126409
0.9084	High Similarity	NPC195022
0.9084	High Similarity	NPC256262
0.9084	High Similarity	NPC134968
0.9084	High Similarity	NPC473413
0.9084	High Similarity	NPC99572
0.9077	High Similarity	NPC49074
0.9077	High Similarity	NPC69513

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 NPC210623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	859
0.2-0.3	1904
0.3-0.4	2702
0.4-0.5	1589
0.5-0.6	917
0.6-0.7	665
0.7-0.8	179
0.8-0.85	11
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.952	High Similarity	NPD3027	Phase 3
0.9147	High Similarity	NPD1613	Approved
0.9147	High Similarity	NPD1612	Clinical (unspecified phase)
0.8837	High Similarity	NPD1529	Clinical (unspecified phase)
0.876	High Similarity	NPD1530	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD2983	Phase 2
0.845	Intermediate Similarity	NPD2982	Phase 2
0.8372	Intermediate Similarity	NPD2981	Phase 2
0.8333	Intermediate Similarity	NPD3018	Phase 2
0.8271	Intermediate Similarity	NPD4908	Phase 1
0.8268	Intermediate Similarity	NPD1548	Phase 1
0.8163	Intermediate Similarity	NPD1934	Approved
0.816	Intermediate Similarity	NPD5283	Phase 1
0.8154	Intermediate Similarity	NPD1610	Phase 2
0.8148	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8145	Intermediate Similarity	NPD228	Approved
0.8049	Intermediate Similarity	NPD2684	Approved
0.8027	Intermediate Similarity	NPD4678	Approved
0.8027	Intermediate Similarity	NPD4675	Approved
0.8015	Intermediate Similarity	NPD1091	Approved
0.8014	Intermediate Similarity	NPD1653	Approved
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2801	Approved
0.7937	Intermediate Similarity	NPD7843	Approved
0.7926	Intermediate Similarity	NPD2861	Phase 2
0.7899	Intermediate Similarity	NPD1558	Phase 1
0.7895	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD7157	Approved
0.7883	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3882	Suspended
0.7879	Intermediate Similarity	NPD3705	Approved
0.7871	Intermediate Similarity	NPD6166	Phase 2
0.7871	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4538	Approved
0.7857	Intermediate Similarity	NPD4536	Approved
0.7857	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD290	Approved
0.7815	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3817	Phase 2
0.781	Intermediate Similarity	NPD4625	Phase 3
0.78	Intermediate Similarity	NPD37	Approved
0.7786	Intermediate Similarity	NPD1357	Approved
0.7763	Intermediate Similarity	NPD4965	Approved
0.7763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4966	Approved
0.7763	Intermediate Similarity	NPD4967	Phase 2
0.7761	Intermediate Similarity	NPD4749	Approved
0.7754	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1511	Approved
0.7722	Intermediate Similarity	NPD7054	Approved
0.7718	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4236	Phase 3
0.7708	Intermediate Similarity	NPD4237	Approved
0.7708	Intermediate Similarity	NPD1652	Phase 2
0.7708	Intermediate Similarity	NPD6674	Discontinued
0.7708	Intermediate Similarity	NPD4162	Approved
0.7708	Intermediate Similarity	NPD3060	Approved
0.7705	Intermediate Similarity	NPD291	Approved
0.7692	Intermediate Similarity	NPD3540	Phase 1
0.7692	Intermediate Similarity	NPD7266	Discontinued
0.7687	Intermediate Similarity	NPD4123	Phase 3
0.7677	Intermediate Similarity	NPD7199	Phase 2
0.7676	Intermediate Similarity	NPD5588	Approved
0.7676	Intermediate Similarity	NPD5960	Phase 3
0.7673	Intermediate Similarity	NPD7074	Phase 3
0.7673	Intermediate Similarity	NPD7472	Approved
0.7662	Intermediate Similarity	NPD6234	Discontinued
0.7658	Intermediate Similarity	NPD3818	Discontinued
0.7643	Intermediate Similarity	NPD3620	Phase 2
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1512	Approved
0.7634	Intermediate Similarity	NPD5536	Phase 2
0.7622	Intermediate Similarity	NPD3539	Phase 1
0.7619	Intermediate Similarity	NPD4357	Discontinued
0.7612	Intermediate Similarity	NPD422	Phase 1
0.761	Intermediate Similarity	NPD5844	Phase 1
0.7609	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2677	Approved
0.76	Intermediate Similarity	NPD968	Approved
0.76	Intermediate Similarity	NPD4005	Discontinued
0.7597	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5846	Approved
0.7594	Intermediate Similarity	NPD6516	Phase 2
0.7591	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD8651	Approved
0.7571	Intermediate Similarity	NPD6233	Phase 2
0.7559	Intermediate Similarity	NPD3022	Approved
0.7559	Intermediate Similarity	NPD3021	Approved
0.7556	Intermediate Similarity	NPD2231	Phase 2
0.7556	Intermediate Similarity	NPD2235	Phase 2
0.7551	Intermediate Similarity	NPD5058	Phase 3
0.7534	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD3687	Approved
0.7533	Intermediate Similarity	NPD3686	Approved
0.7531	Intermediate Similarity	NPD7808	Phase 3
0.7517	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD2219	Phase 1
0.7481	Intermediate Similarity	NPD6671	Approved
0.748	Intermediate Similarity	NPD1242	Phase 1
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5177	Phase 3
0.7465	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5735	Approved
0.7465	Intermediate Similarity	NPD5124	Phase 1
0.7464	Intermediate Similarity	NPD6584	Phase 3
0.7448	Intermediate Similarity	NPD1375	Discontinued
0.7447	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7228	Approved
0.7434	Intermediate Similarity	NPD4380	Phase 2
0.7432	Intermediate Similarity	NPD7124	Phase 2
0.7429	Intermediate Similarity	NPD7095	Approved
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4110	Phase 3
0.7415	Intermediate Similarity	NPD6331	Phase 2
0.7415	Intermediate Similarity	NPD3892	Phase 2
0.7413	Intermediate Similarity	NPD6653	Approved
0.7403	Intermediate Similarity	NPD5773	Approved
0.7403	Intermediate Similarity	NPD5772	Approved
0.74	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2238	Phase 2
0.7389	Intermediate Similarity	NPD5494	Approved
0.7383	Intermediate Similarity	NPD1774	Approved
0.7383	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7212	Phase 2
0.7383	Intermediate Similarity	NPD7213	Phase 3
0.7383	Intermediate Similarity	NPD6799	Approved
0.7376	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6190	Approved
0.7355	Intermediate Similarity	NPD5402	Approved
0.7343	Intermediate Similarity	NPD230	Phase 1
0.7343	Intermediate Similarity	NPD6355	Discontinued
0.7343	Intermediate Similarity	NPD4340	Discontinued
0.7333	Intermediate Similarity	NPD7447	Phase 1
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5762	Approved
0.7329	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4062	Phase 3
0.7305	Intermediate Similarity	NPD3179	Approved
0.7305	Intermediate Similarity	NPD3180	Approved
0.7301	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4535	Phase 3
0.729	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2978	Approved
0.729	Intermediate Similarity	NPD2977	Approved
0.7285	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7526	Approved
0.7285	Intermediate Similarity	NPD52	Approved
0.7279	Intermediate Similarity	NPD1549	Phase 2
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7279	Intermediate Similarity	NPD2424	Discontinued
0.7273	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.726	Intermediate Similarity	NPD2796	Approved
0.726	Intermediate Similarity	NPD2161	Phase 2
0.7252	Intermediate Similarity	NPD821	Approved
0.7252	Intermediate Similarity	NPD5535	Approved
0.7248	Intermediate Similarity	NPD5241	Discontinued
0.7246	Intermediate Similarity	NPD6582	Phase 2
0.7246	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6583	Phase 3
0.7244	Intermediate Similarity	NPD2560	Approved
0.7244	Intermediate Similarity	NPD2563	Approved
0.7241	Intermediate Similarity	NPD6111	Discontinued
0.7237	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5403	Approved
0.7226	Intermediate Similarity	NPD6801	Discontinued
0.7212	Intermediate Similarity	NPD7549	Discontinued
0.7211	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2674	Phase 3
0.7192	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7033	Discontinued
0.7192	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3787	Discontinued
0.7188	Intermediate Similarity	NPD6232	Discontinued
0.7185	Intermediate Similarity	NPD1182	Approved
0.7181	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1465	Phase 2
0.7174	Intermediate Similarity	NPD1608	Approved
0.7172	Intermediate Similarity	NPD3052	Approved
0.7172	Intermediate Similarity	NPD3054	Approved
0.7161	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD556	Approved
0.7153	Intermediate Similarity	NPD4140	Approved
0.7152	Intermediate Similarity	NPD7240	Approved
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD940	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD6099	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