NPASS Compound

Structure

NPC473062 OpenBabel07101718282D 45 51 0 0 1 0 0 0 0 0999 V2000 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6321 -0.2410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0027 -1.0182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8517 -2.3785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -0.1910 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8721 0.1017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0950 -0.5276 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 -0.8660 0.5000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7108 -0.4430 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6444 -0.0846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 -1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5685 -3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4048 -3.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8008 0.9031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4520 -1.4089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 6 32 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 31 1 0 0 0 0 13 34 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 43 1 0 0 0 0 16 34 1 0 0 0 0 16 35 1 0 0 0 0 17 23 1 0 0 0 0 17 36 1 1 0 0 0 18 29 1 0 0 0 0 18 34 1 6 0 0 0 19 32 1 1 0 0 0 19 35 1 0 0 0 0 20 33 1 1 0 0 0 20 37 1 0 0 0 0 21 29 1 0 0 0 0 21 44 1 6 0 0 0 22 30 1 1 0 0 0 22 45 1 0 0 0 0 23 24 1 0 0 0 0 23 38 1 6 0 0 0 24 28 1 0 0 0 0 24 39 1 1 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 25 40 2 0 0 0 0 26 31 1 0 0 0 0 26 33 1 6 0 0 0 27 32 1 1 0 0 0 27 41 1 0 0 0 0 28 43 1 0 0 0 0 28 44 1 6 0 0 0 30 42 1 0 0 0 0 31 5 1 6 0 0 0 31 45 1 0 0 0 0 32 33 1 1 0 0 0 33 7 1 6 0 0 0 34 35 1 1 0 0 0 35 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.39
Volume:	639.287
LogP:	2.436
LogD:	1.031
LogS:	-3.256
# Rotatable Bonds:	4
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	6.545
Fsp3:	0.971
Lipinski Rule-of-5:	Rejected
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:	-5.306
MDCK Permeability:	1.9998733478132635e-05
Pgp-inhibitor:	0.512
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.135
30% Bioavailability (F30%):	0.642

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	73.61319732666016%
Volume Distribution (VD):	0.547
Pgp-substrate:	19.373178482055664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.396
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.56
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	1.634
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.686
Carcinogencity:	0.015
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC473062

Natural Product ID:	NPC473062
*Common Name:**	PQIGFWXBYVEORY-OFLVRPKNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PQIGFWXBYVEORY-OFLVRPKNSA-N
Standard InCHI:	InChI=1S/C35H56O10/c1-29(2)18-8-9-19-32(6)27(41)25(40)26(31(5)12-10-22(45-31)30(3,4)42)33(32,7)20(37)14-35(19)16-34(18,35)13-11-21(29)44-28-24(39)23(38)17(36)15-43-28/h17-24,26-28,36-39,41-42H,8-16H2,1-7H3/t17-,18+,19+,20+,21+,22-,23+,24-,26-,27+,28+,31+,32-,33-,34-,35+/m1/s1
SMILES:	O[C@@H]1CO[C@H]([C@@H]([C@H]1O)O)O[C@H]1CC[C@]23[C@H](C1(C)C)CC[C@@H]1[C@@]3(C2)C[C@H](O)[C@]2([C@@]1(C)[C@@H](O)C(=O)[C@@H]2[C@]1(C)CC[C@@H](O1)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608824
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	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

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21742	CELL-LINE	L02	Homo sapiens	EC50	=	78600.0	nM	PMID[540284]

☑ 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 NPC473062 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	582
0.1-0.2	4297
0.2-0.3	9489
0.3-0.4	12447
0.4-0.5	6972
0.5-0.6	4541
0.6-0.7	2998
0.7-0.8	1206
0.8-0.85	124
0.85-0.9	38
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9057	High Similarity	NPC208333
0.9057	High Similarity	NPC227879
0.902	High Similarity	NPC41843
0.9	High Similarity	NPC179429
0.8952	High Similarity	NPC215408
0.8942	High Similarity	NPC34562
0.8932	High Similarity	NPC178853
0.8857	High Similarity	NPC470167
0.8785	High Similarity	NPC92890
0.8785	High Similarity	NPC202898
0.8785	High Similarity	NPC475319
0.8785	High Similarity	NPC472079
0.8762	High Similarity	NPC107385
0.875	High Similarity	NPC477172
0.8727	High Similarity	NPC97002
0.8725	High Similarity	NPC476728
0.8716	High Similarity	NPC469824
0.8704	High Similarity	NPC92297
0.8704	High Similarity	NPC473817
0.8704	High Similarity	NPC220836
0.8704	High Similarity	NPC233433
0.8704	High Similarity	NPC94086
0.8704	High Similarity	NPC273002
0.8692	High Similarity	NPC203974
0.8679	High Similarity	NPC88469
0.8654	High Similarity	NPC20028
0.8649	High Similarity	NPC79193
0.8636	High Similarity	NPC477489
0.8636	High Similarity	NPC477492
0.8627	High Similarity	NPC305808
0.8571	High Similarity	NPC475490
0.8532	High Similarity	NPC228190
0.8532	High Similarity	NPC236753
0.8529	High Similarity	NPC175
0.8491	Intermediate Similarity	NPC470172
0.8491	Intermediate Similarity	NPC310031
0.8491	Intermediate Similarity	NPC80640
0.8491	Intermediate Similarity	NPC80191
0.8476	Intermediate Similarity	NPC80417
0.8462	Intermediate Similarity	NPC472273
0.8447	Intermediate Similarity	NPC473065
0.8447	Intermediate Similarity	NPC473067
0.8447	Intermediate Similarity	NPC473064
0.844	Intermediate Similarity	NPC469826
0.8431	Intermediate Similarity	NPC161035
0.8411	Intermediate Similarity	NPC473406
0.8411	Intermediate Similarity	NPC471253
0.8396	Intermediate Similarity	NPC476512
0.8396	Intermediate Similarity	NPC472081
0.8396	Intermediate Similarity	NPC108227
0.8393	Intermediate Similarity	NPC102619
0.8365	Intermediate Similarity	NPC476510
0.8365	Intermediate Similarity	NPC142264
0.8364	Intermediate Similarity	NPC87393
0.8333	Intermediate Similarity	NPC267637
0.8318	Intermediate Similarity	NPC114700
0.8318	Intermediate Similarity	NPC134967
0.8318	Intermediate Similarity	NPC470029
0.8318	Intermediate Similarity	NPC310138
0.8302	Intermediate Similarity	NPC470030
0.8288	Intermediate Similarity	NPC66513
0.8288	Intermediate Similarity	NPC470622
0.8286	Intermediate Similarity	NPC470028
0.8286	Intermediate Similarity	NPC233649
0.8269	Intermediate Similarity	NPC215570
0.8257	Intermediate Similarity	NPC184805
0.8257	Intermediate Similarity	NPC273189
0.8257	Intermediate Similarity	NPC166079
0.8257	Intermediate Similarity	NPC306776
0.8252	Intermediate Similarity	NPC311246
0.8252	Intermediate Similarity	NPC167644
0.8241	Intermediate Similarity	NPC476837
0.8241	Intermediate Similarity	NPC139181
0.8241	Intermediate Similarity	NPC97260
0.8235	Intermediate Similarity	NPC273962
0.8235	Intermediate Similarity	NPC104427
0.8235	Intermediate Similarity	NPC473542
0.8214	Intermediate Similarity	NPC272242
0.8198	Intermediate Similarity	NPC469825
0.819	Intermediate Similarity	NPC193785
0.819	Intermediate Similarity	NPC156377
0.819	Intermediate Similarity	NPC116683
0.8182	Intermediate Similarity	NPC471430
0.8173	Intermediate Similarity	NPC45959
0.8173	Intermediate Similarity	NPC113500
0.8173	Intermediate Similarity	NPC30687
0.8173	Intermediate Similarity	NPC151214
0.8173	Intermediate Similarity	NPC252253
0.8173	Intermediate Similarity	NPC191915
0.8173	Intermediate Similarity	NPC477224
0.8173	Intermediate Similarity	NPC3538
0.8167	Intermediate Similarity	NPC292290
0.8167	Intermediate Similarity	NPC2757
0.8165	Intermediate Similarity	NPC100078
0.8165	Intermediate Similarity	NPC469827
0.8158	Intermediate Similarity	NPC470115
0.8158	Intermediate Similarity	NPC470116
0.8155	Intermediate Similarity	NPC149966
0.8155	Intermediate Similarity	NPC5632
0.8148	Intermediate Similarity	NPC213528
0.8148	Intermediate Similarity	NPC244969
0.8148	Intermediate Similarity	NPC471254
0.8137	Intermediate Similarity	NPC82955
0.8125	Intermediate Similarity	NPC106760
0.8113	Intermediate Similarity	NPC471241
0.8113	Intermediate Similarity	NPC475207
0.8077	Intermediate Similarity	NPC473726
0.8077	Intermediate Similarity	NPC144790
0.8077	Intermediate Similarity	NPC88962
0.8077	Intermediate Similarity	NPC149400
0.807	Intermediate Similarity	NPC73986
0.8058	Intermediate Similarity	NPC279329
0.8056	Intermediate Similarity	NPC475574
0.8056	Intermediate Similarity	NPC476839
0.8056	Intermediate Similarity	NPC476838
0.8039	Intermediate Similarity	NPC281004
0.8037	Intermediate Similarity	NPC253995
0.8036	Intermediate Similarity	NPC8431
0.8019	Intermediate Similarity	NPC252056
0.8019	Intermediate Similarity	NPC304011
0.8019	Intermediate Similarity	NPC203434
0.8019	Intermediate Similarity	NPC139271
0.8019	Intermediate Similarity	NPC238796
0.8019	Intermediate Similarity	NPC237071
0.8019	Intermediate Similarity	NPC475765
0.8019	Intermediate Similarity	NPC475785
0.8	Intermediate Similarity	NPC473774
0.8	Intermediate Similarity	NPC473851
0.8	Intermediate Similarity	NPC312678
0.8	Intermediate Similarity	NPC174024
0.8	Intermediate Similarity	NPC327093
0.8	Intermediate Similarity	NPC291547
0.8	Intermediate Similarity	NPC253268
0.8	Intermediate Similarity	NPC477465
0.8	Intermediate Similarity	NPC179859
0.8	Intermediate Similarity	NPC206878
0.8	Intermediate Similarity	NPC475436
0.8	Intermediate Similarity	NPC24960
0.8	Intermediate Similarity	NPC131693
0.7983	Intermediate Similarity	NPC131824
0.7982	Intermediate Similarity	NPC243572
0.7982	Intermediate Similarity	NPC471245
0.7982	Intermediate Similarity	NPC157571
0.7981	Intermediate Similarity	NPC210759
0.7981	Intermediate Similarity	NPC229801
0.7981	Intermediate Similarity	NPC59006
0.7981	Intermediate Similarity	NPC36372
0.7981	Intermediate Similarity	NPC293609
0.7981	Intermediate Similarity	NPC307167
0.7966	Intermediate Similarity	NPC108072
0.7961	Intermediate Similarity	NPC228059
0.7961	Intermediate Similarity	NPC473472
0.7961	Intermediate Similarity	NPC102725
0.7961	Intermediate Similarity	NPC20822
0.7961	Intermediate Similarity	NPC61688
0.7946	Intermediate Similarity	NPC224414
0.7946	Intermediate Similarity	NPC207693
0.7944	Intermediate Similarity	NPC477222
0.7944	Intermediate Similarity	NPC477223
0.7944	Intermediate Similarity	NPC470632
0.7944	Intermediate Similarity	NPC74466
0.7941	Intermediate Similarity	NPC140446
0.7941	Intermediate Similarity	NPC43912
0.7934	Intermediate Similarity	NPC47113
0.7934	Intermediate Similarity	NPC174367
0.7928	Intermediate Similarity	NPC158367
0.7928	Intermediate Similarity	NPC158051
0.7928	Intermediate Similarity	NPC119628
0.7925	Intermediate Similarity	NPC17336
0.7925	Intermediate Similarity	NPC470031
0.7925	Intermediate Similarity	NPC287354
0.7925	Intermediate Similarity	NPC474399
0.7925	Intermediate Similarity	NPC62407
0.7917	Intermediate Similarity	NPC228701
0.7905	Intermediate Similarity	NPC297348
0.7905	Intermediate Similarity	NPC477451
0.7905	Intermediate Similarity	NPC177834
0.7905	Intermediate Similarity	NPC477547
0.7905	Intermediate Similarity	NPC277774
0.7905	Intermediate Similarity	NPC476189
0.7905	Intermediate Similarity	NPC141769
0.7905	Intermediate Similarity	NPC250393
0.7905	Intermediate Similarity	NPC48339
0.7905	Intermediate Similarity	NPC234352
0.7905	Intermediate Similarity	NPC249204
0.7905	Intermediate Similarity	NPC325828
0.7899	Intermediate Similarity	NPC470478
0.7895	Intermediate Similarity	NPC274833
0.7895	Intermediate Similarity	NPC122339
0.7885	Intermediate Similarity	NPC65550
0.7885	Intermediate Similarity	NPC223143
0.7885	Intermediate Similarity	NPC77756
0.7881	Intermediate Similarity	NPC258592
0.7881	Intermediate Similarity	NPC178548
0.7876	Intermediate Similarity	NPC22709
0.787	Intermediate Similarity	NPC473638
0.7869	Intermediate Similarity	NPC305496
0.7863	Intermediate Similarity	NPC473304
0.7857	Intermediate Similarity	NPC475630
0.7857	Intermediate Similarity	NPC40716

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 NPC473062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	617
0.1-0.2	4116
0.2-0.3	2993
0.3-0.4	777
0.4-0.5	329
0.5-0.6	210
0.6-0.7	90
0.7-0.8	17
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD8170	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD8171	Discontinued
0.7805	Intermediate Similarity	NPD7736	Approved
0.7686	Intermediate Similarity	NPD6370	Approved
0.7581	Intermediate Similarity	NPD8293	Discontinued
0.7563	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6059	Approved
0.7521	Intermediate Similarity	NPD6054	Approved
0.746	Intermediate Similarity	NPD7319	Approved
0.7411	Intermediate Similarity	NPD1700	Approved
0.736	Intermediate Similarity	NPD7507	Approved
0.7339	Intermediate Similarity	NPD8328	Phase 3
0.7317	Intermediate Similarity	NPD6016	Approved
0.7317	Intermediate Similarity	NPD6015	Approved
0.7311	Intermediate Similarity	NPD8133	Approved
0.728	Intermediate Similarity	NPD7492	Approved
0.7258	Intermediate Similarity	NPD5988	Approved
0.7255	Intermediate Similarity	NPD6928	Phase 2
0.7222	Intermediate Similarity	NPD6616	Approved
0.7217	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7078	Approved
0.7119	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6412	Phase 2
0.7034	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6033	Approved
0.696	Remote Similarity	NPD6319	Approved
0.6825	Remote Similarity	NPD8294	Approved
0.6825	Remote Similarity	NPD8377	Approved
0.6803	Remote Similarity	NPD6882	Approved
0.6803	Remote Similarity	NPD8297	Approved
0.68	Remote Similarity	NPD7328	Approved
0.68	Remote Similarity	NPD7327	Approved
0.6774	Remote Similarity	NPD6940	Discontinued
0.6772	Remote Similarity	NPD8296	Approved
0.6772	Remote Similarity	NPD8380	Approved
0.6772	Remote Similarity	NPD8379	Approved
0.6772	Remote Similarity	NPD8033	Approved
0.6772	Remote Similarity	NPD8335	Approved
0.6772	Remote Similarity	NPD8378	Approved
0.6765	Remote Similarity	NPD3703	Phase 2
0.6746	Remote Similarity	NPD7516	Approved
0.6731	Remote Similarity	NPD6115	Approved
0.6731	Remote Similarity	NPD6697	Approved
0.6731	Remote Similarity	NPD6118	Approved
0.6731	Remote Similarity	NPD6114	Approved
0.672	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD6372	Approved
0.6694	Remote Similarity	NPD6373	Approved
0.6639	Remote Similarity	NPD4634	Approved
0.6635	Remote Similarity	NPD6116	Phase 1
0.6613	Remote Similarity	NPD4632	Approved
0.6612	Remote Similarity	NPD7320	Approved
0.6585	Remote Similarity	NPD6650	Approved
0.6585	Remote Similarity	NPD6649	Approved
0.6583	Remote Similarity	NPD6675	Approved
0.6583	Remote Similarity	NPD7128	Approved
0.6583	Remote Similarity	NPD6402	Approved
0.6583	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6117	Approved
0.6538	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD7991	Discontinued
0.6512	Remote Similarity	NPD6921	Approved
0.6475	Remote Similarity	NPD6899	Approved
0.6475	Remote Similarity	NPD6881	Approved
0.6471	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8130	Phase 1
0.6446	Remote Similarity	NPD6008	Approved
0.6442	Remote Similarity	NPD3702	Approved
0.6422	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3669	Approved
0.6412	Remote Similarity	NPD6067	Discontinued
0.641	Remote Similarity	NPD4755	Approved
0.6404	Remote Similarity	NPD8034	Phase 2
0.6404	Remote Similarity	NPD8035	Phase 2
0.6393	Remote Similarity	NPD5697	Approved
0.6393	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD1779	Approved
0.6389	Remote Similarity	NPD1780	Approved
0.6385	Remote Similarity	NPD8517	Approved
0.6385	Remote Similarity	NPD8513	Phase 3
0.6385	Remote Similarity	NPD8516	Approved
0.6385	Remote Similarity	NPD8515	Approved
0.6373	Remote Similarity	NPD4244	Approved
0.6373	Remote Similarity	NPD4245	Approved
0.6373	Remote Similarity	NPD4789	Approved
0.6371	Remote Similarity	NPD7102	Approved
0.6371	Remote Similarity	NPD7290	Approved
0.6371	Remote Similarity	NPD6883	Approved
0.6346	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8083	Approved
0.6333	Remote Similarity	NPD8084	Approved
0.6333	Remote Similarity	NPD8138	Approved
0.6333	Remote Similarity	NPD8086	Approved
0.6333	Remote Similarity	NPD8085	Approved
0.6333	Remote Similarity	NPD8139	Approved
0.6333	Remote Similarity	NPD8082	Approved
0.632	Remote Similarity	NPD6869	Approved
0.632	Remote Similarity	NPD6617	Approved
0.632	Remote Similarity	NPD6847	Approved
0.6303	Remote Similarity	NPD5286	Approved
0.6303	Remote Similarity	NPD5285	Approved
0.6303	Remote Similarity	NPD4700	Approved
0.6303	Remote Similarity	NPD4696	Approved
0.629	Remote Similarity	NPD6012	Approved
0.629	Remote Similarity	NPD6014	Approved
0.629	Remote Similarity	NPD6013	Approved
0.6281	Remote Similarity	NPD8276	Approved
0.6281	Remote Similarity	NPD8275	Approved
0.6275	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3698	Phase 2
0.6275	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD5956	Approved
0.623	Remote Similarity	NPD8081	Approved
0.621	Remote Similarity	NPD6011	Approved
0.621	Remote Similarity	NPD6686	Approved
0.6202	Remote Similarity	NPD7115	Discovery
0.6198	Remote Similarity	NPD5211	Phase 2
0.6198	Remote Similarity	NPD5226	Approved
0.6198	Remote Similarity	NPD5225	Approved
0.6198	Remote Similarity	NPD5224	Approved
0.6198	Remote Similarity	NPD4633	Approved
0.6194	Remote Similarity	NPD6336	Discontinued
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD4767	Approved
0.6179	Remote Similarity	NPD4768	Approved
0.6179	Remote Similarity	NPD8393	Approved
0.6176	Remote Similarity	NPD5360	Phase 3
0.6176	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5777	Approved
0.6148	Remote Similarity	NPD5175	Approved
0.6148	Remote Similarity	NPD5174	Approved
0.6116	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD4238	Approved
0.6111	Remote Similarity	NPD4802	Phase 2
0.6098	Remote Similarity	NPD5141	Approved
0.608	Remote Similarity	NPD4729	Approved
0.608	Remote Similarity	NPD4730	Approved
0.6055	Remote Similarity	NPD7329	Approved
0.6038	Remote Similarity	NPD1811	Approved
0.6038	Remote Similarity	NPD1810	Approved
0.6018	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4754	Approved
0.6015	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.5988	Remote Similarity	NPD7799	Discontinued
0.5985	Remote Similarity	NPD7101	Approved
0.5985	Remote Similarity	NPD7100	Approved
0.5984	Remote Similarity	NPD5251	Approved
0.5984	Remote Similarity	NPD5247	Approved
0.5984	Remote Similarity	NPD5248	Approved
0.5984	Remote Similarity	NPD5250	Approved
0.5984	Remote Similarity	NPD5249	Phase 3
0.5966	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5128	Approved
0.5943	Remote Similarity	NPD3181	Approved
0.5935	Remote Similarity	NPD8300	Approved
0.5935	Remote Similarity	NPD8301	Approved
0.5917	Remote Similarity	NPD4697	Phase 3
0.5909	Remote Similarity	NPD6335	Approved
0.5906	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD6908	Approved
0.5896	Remote Similarity	NPD6909	Approved
0.5882	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD8140	Approved
0.5873	Remote Similarity	NPD8307	Discontinued
0.5859	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6081	Approved
0.5849	Remote Similarity	NPD4758	Discontinued
0.5841	Remote Similarity	NPD4788	Approved
0.5833	Remote Similarity	NPD6317	Approved
0.5827	Remote Similarity	NPD8174	Phase 2
0.582	Remote Similarity	NPD5696	Approved
0.582	Remote Similarity	NPD7638	Approved
0.5818	Remote Similarity	NPD5364	Discontinued
0.5818	Remote Similarity	NPD3671	Phase 1
0.5814	Remote Similarity	NPD5217	Approved
0.5814	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5216	Approved
0.5814	Remote Similarity	NPD5215	Approved
0.5812	Remote Similarity	NPD4753	Phase 2
0.5812	Remote Similarity	NPD5328	Approved
0.5798	Remote Similarity	NPD4202	Approved
0.5798	Remote Similarity	NPD6399	Phase 3
0.5797	Remote Similarity	NPD8074	Phase 3
0.5789	Remote Similarity	NPD6314	Approved
0.5789	Remote Similarity	NPD6313	Approved
0.5785	Remote Similarity	NPD5222	Approved
0.5785	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD5221	Approved
0.5781	Remote Similarity	NPD8306	Approved
0.5781	Remote Similarity	NPD8305	Approved
0.5778	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD8418	Phase 2

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