NPASS Compound

Structure

CID16449 OpenBabel06191715342D 30 34 0 0 1 0 0 0 0 0999 V2000 -1.8481 8.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5002 8.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4555 5.1794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 4.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.9605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9051 6.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9778 6.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1076 5.5301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2265 3.4145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2262 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6890 1.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 3.4155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 3.9033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7754 7.7394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3827 4.8779 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6892 0.9766 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3825 3.9028 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5367 2.4395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8460 2.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6912 1.9517 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6909 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8455 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5370 3.4150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0005 1.9522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5555 0.4770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 0.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 17 3 1 1 0 0 0 17 19 1 0 0 0 0 18 28 1 6 0 0 0 19 25 1 6 0 0 0 20 22 1 0 0 0 0 20 25 1 6 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 26 27 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.34
Volume:	459.136
LogP:	6.272
LogD:	5.728
LogS:	-5.743
# Rotatable Bonds:	5
TPSA:	52.99
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	5.199
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.742
MDCK Permeability:	4.9007849156623706e-05
Pgp-inhibitor:	0.388
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	96.5823745727539%
Volume Distribution (VD):	1.343
Pgp-substrate:	1.7956233024597168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.559
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	9.794
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.947
Carcinogencity:	0.043
Eye Corrosion:	0.941
Eye Irritation:	0.541
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC16449

Natural Product ID:	NPC16449
*Common Name:**	NFSVGWISRPLYOZ-POKZUXAFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NFSVGWISRPLYOZ-POKZUXAFSA-N
Standard InCHI:	InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)19-9-10-20-22-21(12-13-25(19,20)4)26(5)14-11-18(28)15-27(26)24(30-27)23(22)29/h16-24,28-29H,6-15H2,1-5H3/t17-,18+,19-,20+,21+,22+,23-,24-,25-,26-,27-/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](C[C@]21[C@@H]([C@@H]3O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497816
PubChem CID:	44583439
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

*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
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1453183]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[18449498]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24767839]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623025]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4070	Eupatorium sternbergianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9636	Micromonospora coerulea	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12496	Elsholtzia blanda	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6821	Tricholoma muscarium	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11588	Astragalus sevangensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10954	Topsentia genitrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1260	Chlorosplenium aeruginosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5679	Topsentia roquensis	Species	n.a.	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1358	Cell Line	LAMA-84	Homo sapiens	IC50	=	7000.0	nM	PMID[469164]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	8300.0	nM	PMID[469164]
NPT1160	Cell Line	BJ	Homo sapiens	IC50	=	19500.0	nM	PMID[469164]

☑ 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 NPC16449 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	473
0.1-0.2	4470
0.2-0.3	12418
0.3-0.4	12053
0.4-0.5	5197
0.5-0.6	4833
0.6-0.7	2499
0.7-0.8	625
0.8-0.85	81
0.85-0.9	38
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC471769
0.9189	High Similarity	NPC10476
0.9189	High Similarity	NPC192501
0.9189	High Similarity	NPC228994
0.9091	High Similarity	NPC477282
0.9091	High Similarity	NPC81074
0.9079	High Similarity	NPC476233
0.9067	High Similarity	NPC158208
0.9067	High Similarity	NPC196136
0.9067	High Similarity	NPC243027
0.8961	High Similarity	NPC147993
0.8947	High Similarity	NPC470145
0.8831	High Similarity	NPC133596
0.8831	High Similarity	NPC302578
0.8831	High Similarity	NPC192046
0.8831	High Similarity	NPC128951
0.8831	High Similarity	NPC474574
0.8831	High Similarity	NPC477227
0.8831	High Similarity	NPC11907
0.8831	High Similarity	NPC105208
0.8831	High Similarity	NPC64081
0.8816	High Similarity	NPC472950
0.8816	High Similarity	NPC472952
0.8816	High Similarity	NPC231680
0.8816	High Similarity	NPC91387
0.8816	High Similarity	NPC270306
0.8765	High Similarity	NPC320824
0.875	High Similarity	NPC475388
0.875	High Similarity	NPC154043
0.875	High Similarity	NPC202688
0.875	High Similarity	NPC60018
0.8718	High Similarity	NPC67657
0.8718	High Similarity	NPC18857
0.8701	High Similarity	NPC163597
0.8667	High Similarity	NPC252182
0.8667	High Similarity	NPC470071
0.8667	High Similarity	NPC127283
0.8667	High Similarity	NPC8004
0.8667	High Similarity	NPC1340
0.8667	High Similarity	NPC187471
0.8659	High Similarity	NPC266651
0.8608	High Similarity	NPC287452
0.859	High Similarity	NPC185915
0.8571	High Similarity	NPC317242
0.8571	High Similarity	NPC473436
0.8554	High Similarity	NPC215968
0.8554	High Similarity	NPC155531
0.8553	High Similarity	NPC473238
0.8553	High Similarity	NPC472341
0.8537	High Similarity	NPC86238
0.8442	Intermediate Similarity	NPC304499
0.8442	Intermediate Similarity	NPC470151
0.8434	Intermediate Similarity	NPC290612
0.8421	Intermediate Similarity	NPC195530
0.8421	Intermediate Similarity	NPC157777
0.8421	Intermediate Similarity	NPC131506
0.84	Intermediate Similarity	NPC241085
0.84	Intermediate Similarity	NPC299948
0.84	Intermediate Similarity	NPC470830
0.84	Intermediate Similarity	NPC470833
0.84	Intermediate Similarity	NPC66407
0.84	Intermediate Similarity	NPC107919
0.8375	Intermediate Similarity	NPC269333
0.8353	Intermediate Similarity	NPC128475
0.8333	Intermediate Similarity	NPC477283
0.8333	Intermediate Similarity	NPC471240
0.8312	Intermediate Similarity	NPC153719
0.8312	Intermediate Similarity	NPC470610
0.8289	Intermediate Similarity	NPC231945
0.8289	Intermediate Similarity	NPC282454
0.8276	Intermediate Similarity	NPC293609
0.8272	Intermediate Similarity	NPC472943
0.8272	Intermediate Similarity	NPC186588
0.8272	Intermediate Similarity	NPC472951
0.8235	Intermediate Similarity	NPC210658
0.8235	Intermediate Similarity	NPC5943
0.8235	Intermediate Similarity	NPC140446
0.8235	Intermediate Similarity	NPC43912
0.8235	Intermediate Similarity	NPC161928
0.8235	Intermediate Similarity	NPC202937
0.8222	Intermediate Similarity	NPC476040
0.8222	Intermediate Similarity	NPC476021
0.8222	Intermediate Similarity	NPC474994
0.8205	Intermediate Similarity	NPC48795
0.8205	Intermediate Similarity	NPC475458
0.8193	Intermediate Similarity	NPC470070
0.8193	Intermediate Similarity	NPC85095
0.8193	Intermediate Similarity	NPC211135
0.8193	Intermediate Similarity	NPC111582
0.8193	Intermediate Similarity	NPC216420
0.8193	Intermediate Similarity	NPC478054
0.8193	Intermediate Similarity	NPC477285
0.8182	Intermediate Similarity	NPC277774
0.8182	Intermediate Similarity	NPC473279
0.8182	Intermediate Similarity	NPC157422
0.8182	Intermediate Similarity	NPC127094
0.8182	Intermediate Similarity	NPC109457
0.8182	Intermediate Similarity	NPC100586
0.8171	Intermediate Similarity	NPC473257
0.8161	Intermediate Similarity	NPC279329
0.8158	Intermediate Similarity	NPC254037
0.8158	Intermediate Similarity	NPC129829
0.8158	Intermediate Similarity	NPC477820
0.814	Intermediate Similarity	NPC476379
0.8133	Intermediate Similarity	NPC475884
0.8133	Intermediate Similarity	NPC473230
0.8118	Intermediate Similarity	NPC131365
0.809	Intermediate Similarity	NPC477224
0.809	Intermediate Similarity	NPC3538
0.809	Intermediate Similarity	NPC113500
0.809	Intermediate Similarity	NPC30687
0.8072	Intermediate Similarity	NPC470611
0.8072	Intermediate Similarity	NPC477447
0.8072	Intermediate Similarity	NPC477286
0.8072	Intermediate Similarity	NPC470155
0.8072	Intermediate Similarity	NPC477446
0.8072	Intermediate Similarity	NPC286719
0.8068	Intermediate Similarity	NPC114389
0.8068	Intermediate Similarity	NPC219516
0.8068	Intermediate Similarity	NPC473066
0.8068	Intermediate Similarity	NPC59006
0.8068	Intermediate Similarity	NPC36372
0.8052	Intermediate Similarity	NPC232925
0.8052	Intermediate Similarity	NPC192192
0.8052	Intermediate Similarity	NPC251201
0.8052	Intermediate Similarity	NPC63588
0.8049	Intermediate Similarity	NPC66766
0.8049	Intermediate Similarity	NPC117137
0.8046	Intermediate Similarity	NPC82955
0.8046	Intermediate Similarity	NPC20822
0.8046	Intermediate Similarity	NPC131466
0.8046	Intermediate Similarity	NPC228059
0.8046	Intermediate Similarity	NPC473472
0.8026	Intermediate Similarity	NPC472741
0.8026	Intermediate Similarity	NPC474756
0.8	Intermediate Similarity	NPC273290
0.8	Intermediate Similarity	NPC477494
0.8	Intermediate Similarity	NPC477602
0.8	Intermediate Similarity	NPC473916
0.8	Intermediate Similarity	NPC477601
0.8	Intermediate Similarity	NPC17336
0.8	Intermediate Similarity	NPC232044
0.8	Intermediate Similarity	NPC92196
0.7978	Intermediate Similarity	NPC137461
0.7978	Intermediate Similarity	NPC311246
0.7978	Intermediate Similarity	NPC256104
0.7978	Intermediate Similarity	NPC182740
0.7978	Intermediate Similarity	NPC211845
0.7978	Intermediate Similarity	NPC122083
0.7978	Intermediate Similarity	NPC167644
0.7976	Intermediate Similarity	NPC477978
0.7976	Intermediate Similarity	NPC241959
0.7955	Intermediate Similarity	NPC223143
0.7955	Intermediate Similarity	NPC10274
0.7952	Intermediate Similarity	NPC470156
0.7952	Intermediate Similarity	NPC190940
0.7952	Intermediate Similarity	NPC470154
0.7952	Intermediate Similarity	NPC73515
0.7931	Intermediate Similarity	NPC281004
0.7927	Intermediate Similarity	NPC476176
0.7912	Intermediate Similarity	NPC473287
0.7912	Intermediate Similarity	NPC252056
0.7907	Intermediate Similarity	NPC121981
0.7907	Intermediate Similarity	NPC472745
0.7895	Intermediate Similarity	NPC63190
0.7895	Intermediate Similarity	NPC48079
0.7889	Intermediate Similarity	NPC151214
0.7889	Intermediate Similarity	NPC191915
0.7889	Intermediate Similarity	NPC309866
0.7889	Intermediate Similarity	NPC175
0.7889	Intermediate Similarity	NPC473503
0.7882	Intermediate Similarity	NPC474156
0.7882	Intermediate Similarity	NPC227260
0.7875	Intermediate Similarity	NPC186851
0.7867	Intermediate Similarity	NPC41577
0.7867	Intermediate Similarity	NPC473276
0.7867	Intermediate Similarity	NPC472946
0.7867	Intermediate Similarity	NPC474380
0.7865	Intermediate Similarity	NPC473830
0.7865	Intermediate Similarity	NPC5632
0.7865	Intermediate Similarity	NPC204881
0.7865	Intermediate Similarity	NPC149966
0.7865	Intermediate Similarity	NPC229801
0.7865	Intermediate Similarity	NPC210759
0.7865	Intermediate Similarity	NPC307167
0.7857	Intermediate Similarity	NPC477284
0.7841	Intermediate Similarity	NPC102725
0.7838	Intermediate Similarity	NPC114891
0.7831	Intermediate Similarity	NPC474714
0.7826	Intermediate Similarity	NPC477223
0.7826	Intermediate Similarity	NPC477222
0.7816	Intermediate Similarity	NPC263802
0.7816	Intermediate Similarity	NPC472396
0.7805	Intermediate Similarity	NPC471045
0.7805	Intermediate Similarity	NPC177343
0.7805	Intermediate Similarity	NPC31828
0.7802	Intermediate Similarity	NPC57964
0.7802	Intermediate Similarity	NPC94582
0.7802	Intermediate Similarity	NPC469710
0.7802	Intermediate Similarity	NPC473064

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 NPC16449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	479
0.1-0.2	4343
0.2-0.3	3013
0.3-0.4	736
0.4-0.5	293
0.5-0.6	208
0.6-0.7	66
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD371	Approved
0.7619	Intermediate Similarity	NPD6928	Phase 2
0.7391	Intermediate Similarity	NPD8171	Discontinued
0.7375	Intermediate Similarity	NPD4787	Phase 1
0.7176	Intermediate Similarity	NPD6118	Approved
0.7176	Intermediate Similarity	NPD6115	Approved
0.7176	Intermediate Similarity	NPD6114	Approved
0.7176	Intermediate Similarity	NPD6697	Approved
0.7073	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6116	Phase 1
0.7024	Intermediate Similarity	NPD3703	Phase 2
0.7011	Intermediate Similarity	NPD7525	Registered
0.6941	Remote Similarity	NPD6117	Approved
0.6905	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7524	Approved
0.6829	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5360	Phase 3
0.67	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4244	Approved
0.6548	Remote Similarity	NPD4245	Approved
0.6548	Remote Similarity	NPD4789	Approved
0.6535	Remote Similarity	NPD1700	Approved
0.6522	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1810	Approved
0.6512	Remote Similarity	NPD1811	Approved
0.6486	Remote Similarity	NPD7516	Approved
0.6429	Remote Similarity	NPD3698	Phase 2
0.6413	Remote Similarity	NPD6695	Phase 3
0.6396	Remote Similarity	NPD7328	Approved
0.6396	Remote Similarity	NPD7327	Approved
0.6383	Remote Similarity	NPD8308	Discontinued
0.6364	Remote Similarity	NPD7991	Discontinued
0.6341	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7645	Phase 2
0.6321	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6700	Approved
0.6289	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4758	Discontinued
0.6277	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6930	Phase 2
0.6264	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD3702	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6228	Remote Similarity	NPD8378	Approved
0.6228	Remote Similarity	NPD8296	Approved
0.6228	Remote Similarity	NPD8380	Approved
0.6228	Remote Similarity	NPD8335	Approved
0.6228	Remote Similarity	NPD8379	Approved
0.6224	Remote Similarity	NPD8035	Phase 2
0.6224	Remote Similarity	NPD8034	Phase 2
0.6224	Remote Similarity	NPD6703	Approved
0.6224	Remote Similarity	NPD6702	Approved
0.6222	Remote Similarity	NPD3671	Phase 1
0.6204	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD8133	Approved
0.618	Remote Similarity	NPD6933	Approved
0.6176	Remote Similarity	NPD7638	Approved
0.6163	Remote Similarity	NPD2254	Approved
0.6163	Remote Similarity	NPD2686	Approved
0.6163	Remote Similarity	NPD2687	Approved
0.6154	Remote Similarity	NPD6929	Approved
0.6146	Remote Similarity	NPD7750	Discontinued
0.614	Remote Similarity	NPD8294	Approved
0.614	Remote Similarity	NPD8377	Approved
0.6118	Remote Similarity	NPD6705	Phase 1
0.6117	Remote Similarity	NPD7639	Approved
0.6117	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD6932	Approved
0.6092	Remote Similarity	NPD5777	Approved
0.6087	Remote Similarity	NPD4748	Discontinued
0.6087	Remote Similarity	NPD8033	Approved
0.6071	Remote Similarity	NPD6940	Discontinued
0.6044	Remote Similarity	NPD5364	Discontinued
0.6019	Remote Similarity	NPD8174	Phase 2
0.6	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7632	Discontinued
0.5979	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6683	Phase 2
0.5963	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6926	Approved
0.5955	Remote Similarity	NPD6924	Approved
0.5938	Remote Similarity	NPD6893	Approved
0.5934	Remote Similarity	NPD5776	Phase 2
0.5934	Remote Similarity	NPD6925	Approved
0.5926	Remote Similarity	NPD6412	Phase 2
0.5926	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7514	Phase 3
0.5909	Remote Similarity	NPD6081	Approved
0.5905	Remote Similarity	NPD5344	Discontinued
0.59	Remote Similarity	NPD7087	Discontinued
0.5895	Remote Similarity	NPD3669	Approved
0.5895	Remote Similarity	NPD4788	Approved
0.5895	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4632	Approved
0.5882	Remote Similarity	NPD7507	Approved
0.5882	Remote Similarity	NPD4224	Phase 2
0.5877	Remote Similarity	NPD7115	Discovery
0.587	Remote Similarity	NPD7145	Approved
0.5868	Remote Similarity	NPD7319	Approved
0.5862	Remote Similarity	NPD6319	Approved
0.5862	Remote Similarity	NPD6059	Approved
0.5862	Remote Similarity	NPD6054	Approved
0.5859	Remote Similarity	NPD5328	Approved
0.5851	Remote Similarity	NPD6902	Approved
0.5842	Remote Similarity	NPD4202	Approved
0.5833	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD7128	Approved
0.5833	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD6402	Approved
0.5833	Remote Similarity	NPD5739	Approved
0.5812	Remote Similarity	NPD7503	Approved
0.5811	Remote Similarity	NPD385	Approved
0.5811	Remote Similarity	NPD384	Approved
0.581	Remote Similarity	NPD8418	Phase 2
0.5804	Remote Similarity	NPD8297	Approved
0.58	Remote Similarity	NPD3168	Discontinued
0.5769	Remote Similarity	NPD4755	Approved
0.5766	Remote Similarity	NPD4634	Approved
0.5763	Remote Similarity	NPD6370	Approved
0.5745	Remote Similarity	NPD7509	Discontinued
0.5745	Remote Similarity	NPD7332	Phase 2
0.5743	Remote Similarity	NPD6079	Approved
0.573	Remote Similarity	NPD4243	Approved
0.5727	Remote Similarity	NPD6899	Approved
0.5727	Remote Similarity	NPD6881	Approved
0.5727	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD3618	Phase 1
0.5714	Remote Similarity	NPD7604	Phase 2
0.5688	Remote Similarity	NPD6008	Approved
0.5686	Remote Similarity	NPD6399	Phase 3
0.5684	Remote Similarity	NPD6898	Phase 1
0.5678	Remote Similarity	NPD6921	Approved
0.5678	Remote Similarity	NPD6015	Approved
0.5678	Remote Similarity	NPD6016	Approved
0.5676	Remote Similarity	NPD388	Approved
0.5676	Remote Similarity	NPD6373	Approved
0.5676	Remote Similarity	NPD6372	Approved
0.5676	Remote Similarity	NPD386	Approved
0.5667	Remote Similarity	NPD7492	Approved
0.566	Remote Similarity	NPD5285	Approved
0.566	Remote Similarity	NPD4696	Approved
0.566	Remote Similarity	NPD4700	Approved
0.566	Remote Similarity	NPD5286	Approved
0.5656	Remote Similarity	NPD7736	Approved
0.5636	Remote Similarity	NPD5697	Approved
0.5636	Remote Similarity	NPD5701	Approved
0.563	Remote Similarity	NPD5988	Approved
0.5625	Remote Similarity	NPD6883	Approved
0.5625	Remote Similarity	NPD7290	Approved
0.5625	Remote Similarity	NPD7102	Approved
0.5625	Remote Similarity	NPD3667	Approved
0.562	Remote Similarity	NPD6616	Approved
0.5619	Remote Similarity	NPD7920	Phase 3
0.5619	Remote Similarity	NPD7919	Phase 3
0.5604	Remote Similarity	NPD4784	Approved
0.5604	Remote Similarity	NPD4785	Approved
0.5603	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD6009	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