NPASS Compound

Structure

NPC473163 OpenBabel07101719132D 38 41 0 0 1 0 0 0 0 0999 V2000 0.5769 -2.9317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0899 -5.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8935 2.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8697 2.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0231 -2.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8201 -3.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3971 0.8918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1849 -2.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9284 0.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2301 -2.2063 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1351 -4.9915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5022 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4866 -3.3376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2270 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9284 -1.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4414 -3.5406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0946 -2.8151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4819 -5.7170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4784 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7431 -4.4690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7930 -1.8867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8334 -4.0631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 17 32 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 26 2 0 0 0 0 20 32 1 0 0 0 0 21 26 1 0 0 0 0 21 34 2 0 0 0 0 22 16 1 1 0 0 0 22 27 1 0 0 0 0 22 38 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 6 0 0 0 24 30 1 1 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 27 29 1 0 0 0 0 27 36 1 1 0 0 0 29 37 1 0 0 0 0 30 7 1 6 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.35
Volume:	567.361
LogP:	3.663
LogD:	3.163
LogS:	-4.455
# Rotatable Bonds:	7
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	5.245
Fsp3:	0.781
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.18
MDCK Permeability:	2.9307291697477922e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	90.66903686523438%
Volume Distribution (VD):	0.945
Pgp-substrate:	7.788652420043945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.879

ADMET: Excretion

Clearance (CL):	4.342
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.764
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.18
Carcinogencity:	0.646
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC473163

Natural Product ID:	NPC473163
*Common Name:**	QFRHSOZLXIIAOY-SUQVKKFHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QFRHSOZLXIIAOY-SUQVKKFHSA-N
Standard InCHI:	InChI=1S/C32H48O6/c1-18(16-22(38-19(2)33)27(36)29(5,6)37)26-20-10-11-24-30(7)14-13-25(35)28(3,4)23(30)12-15-31(24,8)32(20,9)17-21(26)34/h10-11,18,22-24,27,36-37H,12-17H2,1-9H3/t18-,22+,23+,24+,27+,30+,31+,32+/m1/s1
SMILES:	CC(=O)O[C@H]([C@@H](C(O)(C)C)O)C[C@H](C1=C2C=C[C@@H]3[C@]([C@]2(CC1=O)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632943
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
IC50	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	33410.0	nM	PMID[573648]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	12140.0	nM	PMID[573649]

☑ 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 NPC473163 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	202
0.1-0.2	935
0.2-0.3	3901
0.3-0.4	8478
0.4-0.5	13065
0.5-0.6	7256
0.6-0.7	6236
0.7-0.8	2550
0.8-0.85	62
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9271	High Similarity	NPC471582
0.9255	High Similarity	NPC473172
0.9062	High Similarity	NPC473164
0.8835	High Similarity	NPC41405
0.8812	High Similarity	NPC473175
0.88	High Similarity	NPC473928
0.875	High Similarity	NPC5284
0.8713	High Similarity	NPC264048
0.866	High Similarity	NPC473162
0.8627	High Similarity	NPC255309
0.86	High Similarity	NPC167974
0.8585	High Similarity	NPC234042
0.8585	High Similarity	NPC152117
0.8571	High Similarity	NPC473170
0.8544	High Similarity	NPC96377
0.8515	High Similarity	NPC473174
0.8515	High Similarity	NPC469327
0.8505	High Similarity	NPC255017
0.8476	Intermediate Similarity	NPC475065
0.8462	Intermediate Similarity	NPC473284
0.84	Intermediate Similarity	NPC473161
0.8396	Intermediate Similarity	NPC239097
0.8384	Intermediate Similarity	NPC473415
0.8384	Intermediate Similarity	NPC30677
0.8384	Intermediate Similarity	NPC37787
0.8384	Intermediate Similarity	NPC469329
0.8384	Intermediate Similarity	NPC180557
0.8381	Intermediate Similarity	NPC475418
0.8381	Intermediate Similarity	NPC318363
0.8381	Intermediate Similarity	NPC473482
0.8333	Intermediate Similarity	NPC115899
0.8317	Intermediate Similarity	NPC471717
0.83	Intermediate Similarity	NPC471153
0.83	Intermediate Similarity	NPC471039
0.83	Intermediate Similarity	NPC471775
0.8286	Intermediate Similarity	NPC329048
0.8286	Intermediate Similarity	NPC330011
0.8286	Intermediate Similarity	NPC475294
0.8286	Intermediate Similarity	NPC9457
0.8286	Intermediate Similarity	NPC471783
0.8283	Intermediate Similarity	NPC67831
0.8283	Intermediate Similarity	NPC174051
0.8283	Intermediate Similarity	NPC240617
0.8269	Intermediate Similarity	NPC471293
0.8265	Intermediate Similarity	NPC19114
0.8265	Intermediate Similarity	NPC262870
0.8252	Intermediate Similarity	NPC114540
0.8252	Intermediate Similarity	NPC32577
0.8252	Intermediate Similarity	NPC155332
0.8235	Intermediate Similarity	NPC266955
0.8229	Intermediate Similarity	NPC90652
0.8224	Intermediate Similarity	NPC37116
0.8224	Intermediate Similarity	NPC29133
0.8224	Intermediate Similarity	NPC473627
0.82	Intermediate Similarity	NPC88310
0.82	Intermediate Similarity	NPC139459
0.819	Intermediate Similarity	NPC181265
0.8182	Intermediate Similarity	NPC79117
0.8173	Intermediate Similarity	NPC239716
0.8173	Intermediate Similarity	NPC72151
0.8173	Intermediate Similarity	NPC475050
0.8148	Intermediate Similarity	NPC470961
0.8144	Intermediate Similarity	NPC44181
0.8144	Intermediate Similarity	NPC470417
0.8131	Intermediate Similarity	NPC310546
0.8131	Intermediate Similarity	NPC170221
0.8131	Intermediate Similarity	NPC10064
0.8125	Intermediate Similarity	NPC324063
0.8125	Intermediate Similarity	NPC473168
0.8119	Intermediate Similarity	NPC471777
0.8119	Intermediate Similarity	NPC471822
0.8113	Intermediate Similarity	NPC44063
0.8113	Intermediate Similarity	NPC473169
0.8108	Intermediate Similarity	NPC471854
0.81	Intermediate Similarity	NPC159410
0.81	Intermediate Similarity	NPC49670
0.81	Intermediate Similarity	NPC471078
0.81	Intermediate Similarity	NPC473280
0.81	Intermediate Similarity	NPC473435
0.81	Intermediate Similarity	NPC471040
0.81	Intermediate Similarity	NPC473431
0.8095	Intermediate Similarity	NPC235889
0.8091	Intermediate Similarity	NPC473898
0.8081	Intermediate Similarity	NPC473986
0.8081	Intermediate Similarity	NPC473166
0.8081	Intermediate Similarity	NPC474018
0.8081	Intermediate Similarity	NPC473167
0.8081	Intermediate Similarity	NPC218301
0.8077	Intermediate Similarity	NPC320447
0.8073	Intermediate Similarity	NPC475524
0.8073	Intermediate Similarity	NPC100267
0.8061	Intermediate Similarity	NPC476733
0.8061	Intermediate Similarity	NPC474570
0.8061	Intermediate Similarity	NPC215029
0.8058	Intermediate Similarity	NPC316964
0.8058	Intermediate Similarity	NPC35751
0.8056	Intermediate Similarity	NPC6206
0.8041	Intermediate Similarity	NPC469322
0.8039	Intermediate Similarity	NPC472732
0.8039	Intermediate Similarity	NPC472731
0.8039	Intermediate Similarity	NPC474785
0.8039	Intermediate Similarity	NPC474938
0.8039	Intermediate Similarity	NPC473456
0.8037	Intermediate Similarity	NPC220155
0.8036	Intermediate Similarity	NPC257457
0.8036	Intermediate Similarity	NPC311554
0.8021	Intermediate Similarity	NPC76333
0.802	Intermediate Similarity	NPC470016
0.802	Intermediate Similarity	NPC469599
0.802	Intermediate Similarity	NPC171395
0.802	Intermediate Similarity	NPC317586
0.8019	Intermediate Similarity	NPC266570
0.8019	Intermediate Similarity	NPC196528
0.8019	Intermediate Similarity	NPC102352
0.8018	Intermediate Similarity	NPC270929
0.8	Intermediate Similarity	NPC469463
0.8	Intermediate Similarity	NPC107674
0.8	Intermediate Similarity	NPC473283
0.8	Intermediate Similarity	NPC141497
0.8	Intermediate Similarity	NPC469496
0.8	Intermediate Similarity	NPC475526
0.8	Intermediate Similarity	NPC86370
0.8	Intermediate Similarity	NPC250109
0.8	Intermediate Similarity	NPC469454
0.8	Intermediate Similarity	NPC170220
0.8	Intermediate Similarity	NPC329345
0.7982	Intermediate Similarity	NPC43775
0.7981	Intermediate Similarity	NPC101067
0.7981	Intermediate Similarity	NPC476240
0.7981	Intermediate Similarity	NPC224720
0.7981	Intermediate Similarity	NPC99411
0.7981	Intermediate Similarity	NPC476223
0.7981	Intermediate Similarity	NPC476134
0.7981	Intermediate Similarity	NPC282524
0.798	Intermediate Similarity	NPC471896
0.798	Intermediate Similarity	NPC474842
0.798	Intermediate Similarity	NPC475965
0.798	Intermediate Similarity	NPC289213
0.7979	Intermediate Similarity	NPC327002
0.7965	Intermediate Similarity	NPC270850
0.7965	Intermediate Similarity	NPC305260
0.7965	Intermediate Similarity	NPC161065
0.7963	Intermediate Similarity	NPC472216
0.7963	Intermediate Similarity	NPC246205
0.7963	Intermediate Similarity	NPC2766
0.7963	Intermediate Similarity	NPC5475
0.7963	Intermediate Similarity	NPC258543
0.7963	Intermediate Similarity	NPC173905
0.7963	Intermediate Similarity	NPC241927
0.7963	Intermediate Similarity	NPC284828
0.7963	Intermediate Similarity	NPC304495
0.7963	Intermediate Similarity	NPC153239
0.7961	Intermediate Similarity	NPC203388
0.7961	Intermediate Similarity	NPC57079
0.7961	Intermediate Similarity	NPC472687
0.7961	Intermediate Similarity	NPC99657
0.7961	Intermediate Similarity	NPC114274
0.7961	Intermediate Similarity	NPC471331
0.7961	Intermediate Similarity	NPC471330
0.7961	Intermediate Similarity	NPC108368
0.7959	Intermediate Similarity	NPC97884
0.7959	Intermediate Similarity	NPC310752
0.7959	Intermediate Similarity	NPC255176
0.7959	Intermediate Similarity	NPC292491
0.7959	Intermediate Similarity	NPC472220
0.7946	Intermediate Similarity	NPC470959
0.7946	Intermediate Similarity	NPC312824
0.7946	Intermediate Similarity	NPC284068
0.7946	Intermediate Similarity	NPC476965
0.7946	Intermediate Similarity	NPC470493
0.7946	Intermediate Similarity	NPC183580
0.7944	Intermediate Similarity	NPC220974
0.7944	Intermediate Similarity	NPC144854
0.7944	Intermediate Similarity	NPC59530
0.7944	Intermediate Similarity	NPC3316
0.7941	Intermediate Similarity	NPC472733
0.7941	Intermediate Similarity	NPC111684
0.7941	Intermediate Similarity	NPC328371
0.7941	Intermediate Similarity	NPC301534
0.7941	Intermediate Similarity	NPC58052
0.7941	Intermediate Similarity	NPC230151
0.7941	Intermediate Similarity	NPC250757
0.7941	Intermediate Similarity	NPC472734
0.7938	Intermediate Similarity	NPC195640
0.7938	Intermediate Similarity	NPC325594
0.7938	Intermediate Similarity	NPC73038
0.7938	Intermediate Similarity	NPC89077
0.7928	Intermediate Similarity	NPC471398
0.7925	Intermediate Similarity	NPC75531
0.7925	Intermediate Similarity	NPC13385
0.7925	Intermediate Similarity	NPC149124
0.7921	Intermediate Similarity	NPC166906
0.7921	Intermediate Similarity	NPC184870
0.7921	Intermediate Similarity	NPC74751
0.7921	Intermediate Similarity	NPC318332
0.7917	Intermediate Similarity	NPC85774
0.7917	Intermediate Similarity	NPC214043
0.7909	Intermediate Similarity	NPC474516
0.7909	Intermediate Similarity	NPC470063
0.7909	Intermediate Similarity	NPC191620

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 NPC473163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1177
0.2-0.3	3575
0.3-0.4	2692
0.4-0.5	946
0.5-0.6	267
0.6-0.7	187
0.7-0.8	132
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8411	Intermediate Similarity	NPD8297	Approved
0.8218	Intermediate Similarity	NPD6083	Phase 2
0.8218	Intermediate Similarity	NPD6084	Phase 2
0.8208	Intermediate Similarity	NPD6881	Approved
0.8208	Intermediate Similarity	NPD6899	Approved
0.819	Intermediate Similarity	NPD6402	Approved
0.819	Intermediate Similarity	NPD7128	Approved
0.819	Intermediate Similarity	NPD6675	Approved
0.819	Intermediate Similarity	NPD5739	Approved
0.8148	Intermediate Similarity	NPD8130	Phase 1
0.8113	Intermediate Similarity	NPD5697	Approved
0.8056	Intermediate Similarity	NPD6883	Approved
0.8056	Intermediate Similarity	NPD7102	Approved
0.8056	Intermediate Similarity	NPD7290	Approved
0.8037	Intermediate Similarity	NPD7320	Approved
0.7982	Intermediate Similarity	NPD6649	Approved
0.7982	Intermediate Similarity	NPD6617	Approved
0.7982	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6869	Approved
0.7982	Intermediate Similarity	NPD6650	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.7963	Intermediate Similarity	NPD6014	Approved
0.7963	Intermediate Similarity	NPD6013	Approved
0.7963	Intermediate Similarity	NPD6012	Approved
0.7963	Intermediate Similarity	NPD6373	Approved
0.7944	Intermediate Similarity	NPD5701	Approved
0.7938	Intermediate Similarity	NPD6684	Approved
0.7938	Intermediate Similarity	NPD7146	Approved
0.7938	Intermediate Similarity	NPD7521	Approved
0.7938	Intermediate Similarity	NPD7334	Approved
0.7938	Intermediate Similarity	NPD6409	Approved
0.7938	Intermediate Similarity	NPD5330	Approved
0.7921	Intermediate Similarity	NPD7748	Approved
0.7909	Intermediate Similarity	NPD6882	Approved
0.79	Intermediate Similarity	NPD6411	Approved
0.79	Intermediate Similarity	NPD6079	Approved
0.7879	Intermediate Similarity	NPD5328	Approved
0.787	Intermediate Similarity	NPD6011	Approved
0.7843	Intermediate Similarity	NPD5695	Phase 3
0.7838	Intermediate Similarity	NPD4632	Approved
0.7822	Intermediate Similarity	NPD6399	Phase 3
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7788	Intermediate Similarity	NPD5696	Approved
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7778	Intermediate Similarity	NPD6903	Approved
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7778	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6319	Approved
0.7732	Intermediate Similarity	NPD3665	Phase 1
0.7732	Intermediate Similarity	NPD3666	Approved
0.7732	Intermediate Similarity	NPD3133	Approved
0.7723	Intermediate Similarity	NPD7515	Phase 2
0.7723	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD5281	Approved
0.7714	Intermediate Similarity	NPD5286	Approved
0.7714	Intermediate Similarity	NPD4696	Approved
0.7714	Intermediate Similarity	NPD5285	Approved
0.77	Intermediate Similarity	NPD4753	Phase 2
0.77	Intermediate Similarity	NPD6101	Approved
0.77	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4755	Approved
0.7692	Intermediate Similarity	NPD7902	Approved
0.7658	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5222	Approved
0.7596	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5279	Phase 3
0.7576	Intermediate Similarity	NPD3618	Phase 1
0.757	Intermediate Similarity	NPD5224	Approved
0.757	Intermediate Similarity	NPD4633	Approved
0.757	Intermediate Similarity	NPD5226	Approved
0.757	Intermediate Similarity	NPD5211	Phase 2
0.757	Intermediate Similarity	NPD5225	Approved
0.7551	Intermediate Similarity	NPD4786	Approved
0.7549	Intermediate Similarity	NPD5694	Approved
0.7549	Intermediate Similarity	NPD6050	Approved
0.7547	Intermediate Similarity	NPD4700	Approved
0.7526	Intermediate Similarity	NPD3667	Approved
0.7525	Intermediate Similarity	NPD6673	Approved
0.7525	Intermediate Similarity	NPD6080	Approved
0.7525	Intermediate Similarity	NPD6904	Approved
0.7524	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7479	Intermediate Similarity	NPD7492	Approved
0.7478	Intermediate Similarity	NPD6009	Approved
0.7477	Intermediate Similarity	NPD5223	Approved
0.7451	Intermediate Similarity	NPD5692	Phase 3
0.7451	Intermediate Similarity	NPD5207	Approved
0.7438	Intermediate Similarity	NPD7736	Approved
0.7436	Intermediate Similarity	NPD6054	Approved
0.7431	Intermediate Similarity	NPD5141	Approved
0.7429	Intermediate Similarity	NPD4697	Phase 3
0.7417	Intermediate Similarity	NPD6616	Approved
0.7414	Intermediate Similarity	NPD6335	Approved
0.7411	Intermediate Similarity	NPD4634	Approved
0.7404	Intermediate Similarity	NPD7900	Approved
0.7404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD7604	Phase 2
0.7391	Intermediate Similarity	NPD6274	Approved
0.7391	Intermediate Similarity	NPD6868	Approved
0.7387	Intermediate Similarity	NPD6686	Approved
0.7373	Intermediate Similarity	NPD5983	Phase 2
0.7355	Intermediate Similarity	NPD7078	Approved
0.7355	Intermediate Similarity	NPD8293	Discontinued
0.7353	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4223	Phase 3
0.7347	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6317	Approved
0.7311	Intermediate Similarity	NPD6370	Approved
0.7308	Intermediate Similarity	NPD5778	Approved
0.7308	Intermediate Similarity	NPD5779	Approved
0.7308	Intermediate Similarity	NPD4202	Approved
0.73	Intermediate Similarity	NPD5329	Approved
0.729	Intermediate Similarity	NPD7638	Approved
0.7288	Intermediate Similarity	NPD6059	Approved
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7265	Intermediate Similarity	NPD6313	Approved
0.7265	Intermediate Similarity	NPD6314	Approved
0.7255	Intermediate Similarity	NPD5208	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3
0.7232	Intermediate Similarity	NPD4729	Approved
0.7232	Intermediate Similarity	NPD4730	Approved
0.7228	Intermediate Similarity	NPD4623	Approved
0.7228	Intermediate Similarity	NPD4519	Discontinued
0.7228	Intermediate Similarity	NPD4694	Approved
0.7228	Intermediate Similarity	NPD5280	Approved
0.7228	Intermediate Similarity	NPD6098	Approved
0.7227	Intermediate Similarity	NPD6016	Approved
0.7227	Intermediate Similarity	NPD6908	Approved
0.7227	Intermediate Similarity	NPD6909	Approved
0.7227	Intermediate Similarity	NPD6015	Approved
0.7222	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD7640	Approved
0.7212	Intermediate Similarity	NPD5693	Phase 1
0.7207	Intermediate Similarity	NPD4768	Approved
0.7207	Intermediate Similarity	NPD4767	Approved
0.7207	Intermediate Similarity	NPD6008	Approved
0.72	Intermediate Similarity	NPD4197	Approved
0.7182	Intermediate Similarity	NPD4754	Approved
0.7172	Intermediate Similarity	NPD6435	Approved
0.7168	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5988	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.7105	Intermediate Similarity	NPD5247	Approved
0.7105	Intermediate Similarity	NPD5251	Approved
0.7105	Intermediate Similarity	NPD5248	Approved
0.7105	Intermediate Similarity	NPD5249	Phase 3
0.7105	Intermediate Similarity	NPD5250	Approved
0.7083	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5128	Approved
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4689	Approved
0.7059	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4690	Approved
0.7059	Intermediate Similarity	NPD5205	Approved
0.7059	Intermediate Similarity	NPD5690	Phase 2
0.7059	Intermediate Similarity	NPD4688	Approved
0.7059	Intermediate Similarity	NPD4138	Approved
0.7059	Intermediate Similarity	NPD4693	Phase 3
0.7048	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD7983	Approved
0.7048	Intermediate Similarity	NPD8035	Phase 2
0.7048	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD5216	Approved
0.7043	Intermediate Similarity	NPD5215	Approved
0.7043	Intermediate Similarity	NPD5217	Approved
0.703	Intermediate Similarity	NPD3668	Phase 3
0.7018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5654	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7524	Approved
0.6983	Remote Similarity	NPD6053	Discontinued
0.697	Remote Similarity	NPD5368	Approved
0.697	Remote Similarity	NPD4695	Discontinued
0.6961	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD5169	Approved
0.6957	Remote Similarity	NPD5135	Approved
0.6957	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7503	Approved
0.6939	Remote Similarity	NPD3617	Approved
0.6931	Remote Similarity	NPD4788	Approved
0.693	Remote Similarity	NPD5168	Approved
0.6916	Remote Similarity	NPD6001	Approved
0.6907	Remote Similarity	NPD6933	Approved
0.6897	Remote Similarity	NPD5127	Approved
0.6881	Remote Similarity	NPD5959	Approved
0.6875	Remote Similarity	NPD4058	Approved
0.6869	Remote Similarity	NPD4195	Approved
0.681	Remote Similarity	NPD5955	Clinical (unspecified phase)

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