NPASS Compound

Structure

NPC472749 OpenBabel07101718302D 34 36 0 0 1 0 0 0 0 0999 V2000 -1.8499 -1.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2991 -2.6659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4285 -1.7387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0568 -3.4753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2013 -3.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7663 -3.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2821 -0.3618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6890 -1.8168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0767 -1.5855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2661 -2.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4198 -0.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2809 -0.6988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.1436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8894 -1.2885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0890 -2.1071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1970 -0.7992 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9679 -2.5118 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5003 -0.2626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8311 -2.1914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1212 -0.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8213 -0.7276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5734 -0.4882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0653 -0.2626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2825 -2.3266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3863 -0.7276 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5650 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7578 -1.9530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0322 0.2246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7260 -0.3845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7069 0.4617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6374 0.9649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3312 -1.2976 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 1.6405 -1.6612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 1 1 6 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 16 3 1 6 0 0 0 16 22 1 0 0 0 0 17 27 1 0 0 0 0 18 12 1 1 0 0 0 18 21 1 0 0 0 0 18 33 1 0 0 0 0 19 9 1 1 0 0 0 19 24 1 0 0 0 0 19 34 1 0 0 0 0 20 28 2 0 0 0 0 20 32 1 0 0 0 0 21 29 2 0 0 0 0 22 26 1 6 0 0 0 22 32 1 0 0 0 0 23 25 1 1 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 25 7 1 1 0 0 0 25 34 1 0 0 0 0 26 31 1 1 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.27
Volume:	492.359
LogP:	3.373
LogD:	0.916
LogS:	-3.067
# Rotatable Bonds:	5
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	6.833
Fsp3:	0.808
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:	-4.699
MDCK Permeability:	1.389078806823818e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.135

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	91.0988998413086%
Volume Distribution (VD):	1.587
Pgp-substrate:	5.850677967071533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.592
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.26
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	7.612
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.734
Maximum Recommended Daily Dose:	0.777
Skin Sensitization:	0.374
Carcinogencity:	0.063
Eye Corrosion:	0.16
Eye Irritation:	0.019
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC472749

Natural Product ID:	NPC472749
*Common Name:**	KPOHXWINICIAQL-SIOPPVCOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KPOHXWINICIAQL-SIOPPVCOSA-N
Standard InCHI:	InChI=1S/C26H40O8/c1-14-8-10-24(5,6)19-9-11-25(7,34-19)23(30)26(31)22(16(3)12-18(33-26)21(14)29)32-20(28)13-15(2)17(4)27/h8,10,13-14,16-19,22-23,27,30-31H,9,11-12H2,1-7H3/b10-8+,15-13+/t14-,16+,17?,18+,19-,22+,23-,25+,26-/m0/s1
SMILES:	O=C(O[C@@H]1[C@H](C)C[C@H]2O[C@]1(O)[C@@H](O)[C@@]1(C)CC[C@H](O1)C(/C=C/[C@@H](C2=O)C)(C)C)/C=C(/C(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581996
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]
NPO40934	Stillingia loranthacea	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31599155]

☑ 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	3
Others	10

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[542456]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[542456]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[542456]
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	=	50.0	%	PMID[542456]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	=	41.0	%	PMID[542456]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	210000.0	nM	PMID[542456]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC20	=	8.7	uM	PMID[542457]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	24600.0	nM	PMID[542457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	24000.0	nM	PMID[542456]
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	=	109000.0	nM	PMID[542456]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	208000.0	nM	PMID[542456]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	9.0	n.a.	PMID[542456]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	1.9	n.a.	PMID[542456]

☑ 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 NPC472749 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	190
0.1-0.2	1082
0.2-0.3	3934
0.3-0.4	7130
0.4-0.5	13602
0.5-0.6	8109
0.6-0.7	6262
0.7-0.8	2303
0.8-0.85	61
0.85-0.9	17
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472751
0.9897	High Similarity	NPC472748
0.9794	High Similarity	NPC472747
0.9794	High Similarity	NPC472750
0.9293	High Similarity	NPC472754
0.92	High Similarity	NPC472755
0.9192	High Similarity	NPC472753
0.8922	High Similarity	NPC472756
0.85	High Similarity	NPC36954
0.8381	Intermediate Similarity	NPC475676
0.8381	Intermediate Similarity	NPC220964
0.8365	Intermediate Similarity	NPC324017
0.8365	Intermediate Similarity	NPC320019
0.8365	Intermediate Similarity	NPC473596
0.8365	Intermediate Similarity	NPC149371
0.8348	Intermediate Similarity	NPC470922
0.8333	Intermediate Similarity	NPC40812
0.8333	Intermediate Similarity	NPC5103
0.8319	Intermediate Similarity	NPC109607
0.8319	Intermediate Similarity	NPC107338
0.8318	Intermediate Similarity	NPC14862
0.8318	Intermediate Similarity	NPC233379
0.8318	Intermediate Similarity	NPC474664
0.8302	Intermediate Similarity	NPC476740
0.8302	Intermediate Similarity	NPC476738
0.83	Intermediate Similarity	NPC476300
0.83	Intermediate Similarity	NPC475912
0.8286	Intermediate Similarity	NPC4620
0.8286	Intermediate Similarity	NPC475945
0.8286	Intermediate Similarity	NPC475871
0.8286	Intermediate Similarity	NPC309398
0.8283	Intermediate Similarity	NPC476004
0.8283	Intermediate Similarity	NPC474761
0.8273	Intermediate Similarity	NPC469463
0.8273	Intermediate Similarity	NPC469454
0.8273	Intermediate Similarity	NPC469496
0.8269	Intermediate Similarity	NPC46998
0.8269	Intermediate Similarity	NPC476270
0.8269	Intermediate Similarity	NPC128733
0.8269	Intermediate Similarity	NPC110443
0.8269	Intermediate Similarity	NPC15993
0.8269	Intermediate Similarity	NPC185141
0.8269	Intermediate Similarity	NPC133907
0.8269	Intermediate Similarity	NPC47880
0.8247	Intermediate Similarity	NPC311163
0.8241	Intermediate Similarity	NPC315836
0.8241	Intermediate Similarity	NPC313668
0.8241	Intermediate Similarity	NPC15218
0.8235	Intermediate Similarity	NPC476315
0.823	Intermediate Similarity	NPC476529
0.823	Intermediate Similarity	NPC475775
0.8224	Intermediate Similarity	NPC474421
0.8224	Intermediate Similarity	NPC324327
0.8224	Intermediate Similarity	NPC72813
0.8224	Intermediate Similarity	NPC326994
0.8224	Intermediate Similarity	NPC194620
0.8218	Intermediate Similarity	NPC71589
0.82	Intermediate Similarity	NPC30515
0.82	Intermediate Similarity	NPC184463
0.819	Intermediate Similarity	NPC474747
0.8163	Intermediate Similarity	NPC179659
0.8148	Intermediate Similarity	NPC327286
0.8148	Intermediate Similarity	NPC169888
0.8148	Intermediate Similarity	NPC55972
0.8137	Intermediate Similarity	NPC270013
0.8137	Intermediate Similarity	NPC14961
0.8131	Intermediate Similarity	NPC9303
0.8131	Intermediate Similarity	NPC16313
0.8131	Intermediate Similarity	NPC475802
0.8125	Intermediate Similarity	NPC152199
0.8125	Intermediate Similarity	NPC259306
0.8125	Intermediate Similarity	NPC470628
0.8125	Intermediate Similarity	NPC134869
0.8125	Intermediate Similarity	NPC474046
0.8125	Intermediate Similarity	NPC235539
0.8119	Intermediate Similarity	NPC273579
0.8119	Intermediate Similarity	NPC162205
0.8119	Intermediate Similarity	NPC295204
0.8119	Intermediate Similarity	NPC288240
0.8113	Intermediate Similarity	NPC474581
0.8113	Intermediate Similarity	NPC475367
0.8113	Intermediate Similarity	NPC473816
0.81	Intermediate Similarity	NPC51004
0.81	Intermediate Similarity	NPC473448
0.8095	Intermediate Similarity	NPC474742
0.8091	Intermediate Similarity	NPC304180
0.8091	Intermediate Similarity	NPC179798
0.8091	Intermediate Similarity	NPC126897
0.8091	Intermediate Similarity	NPC297945
0.8077	Intermediate Similarity	NPC471144
0.8077	Intermediate Similarity	NPC187268
0.8077	Intermediate Similarity	NPC308567
0.8077	Intermediate Similarity	NPC255592
0.8077	Intermediate Similarity	NPC83895
0.8077	Intermediate Similarity	NPC475653
0.8077	Intermediate Similarity	NPC261377
0.8077	Intermediate Similarity	NPC187761
0.8056	Intermediate Similarity	NPC477513
0.8053	Intermediate Similarity	NPC471145
0.8053	Intermediate Similarity	NPC473968
0.8053	Intermediate Similarity	NPC471146
0.8053	Intermediate Similarity	NPC23046
0.8039	Intermediate Similarity	NPC474035
0.8039	Intermediate Similarity	NPC121825
0.8039	Intermediate Similarity	NPC190294
0.8039	Intermediate Similarity	NPC81386
0.8037	Intermediate Similarity	NPC474741
0.8037	Intermediate Similarity	NPC203659
0.8037	Intermediate Similarity	NPC258532
0.8036	Intermediate Similarity	NPC470919
0.8036	Intermediate Similarity	NPC469877
0.8036	Intermediate Similarity	NPC18547
0.8036	Intermediate Similarity	NPC474906
0.802	Intermediate Similarity	NPC470379
0.802	Intermediate Similarity	NPC470373
0.8018	Intermediate Similarity	NPC317687
0.8	Intermediate Similarity	NPC48692
0.8	Intermediate Similarity	NPC161816
0.8	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC115257
0.7982	Intermediate Similarity	NPC193765
0.7982	Intermediate Similarity	NPC473807
0.7982	Intermediate Similarity	NPC297179
0.7981	Intermediate Similarity	NPC120299
0.7981	Intermediate Similarity	NPC328562
0.7981	Intermediate Similarity	NPC323421
0.7959	Intermediate Similarity	NPC471494
0.7951	Intermediate Similarity	NPC471234
0.7949	Intermediate Similarity	NPC67251
0.7946	Intermediate Similarity	NPC51978
0.7946	Intermediate Similarity	NPC56448
0.7944	Intermediate Similarity	NPC110989
0.7941	Intermediate Similarity	NPC469645
0.7941	Intermediate Similarity	NPC212486
0.7941	Intermediate Similarity	NPC469692
0.7941	Intermediate Similarity	NPC81419
0.7941	Intermediate Similarity	NPC179746
0.7941	Intermediate Similarity	NPC11456
0.7931	Intermediate Similarity	NPC473228
0.7931	Intermediate Similarity	NPC470829
0.7928	Intermediate Similarity	NPC317107
0.7925	Intermediate Similarity	NPC472643
0.7925	Intermediate Similarity	NPC474339
0.7925	Intermediate Similarity	NPC201718
0.7925	Intermediate Similarity	NPC164598
0.7913	Intermediate Similarity	NPC477092
0.7909	Intermediate Similarity	NPC475922
0.7909	Intermediate Similarity	NPC38154
0.7909	Intermediate Similarity	NPC273433
0.7905	Intermediate Similarity	NPC203627
0.79	Intermediate Similarity	NPC202672
0.7895	Intermediate Similarity	NPC473590
0.7885	Intermediate Similarity	NPC39859
0.7885	Intermediate Similarity	NPC279621
0.7885	Intermediate Similarity	NPC76862
0.7885	Intermediate Similarity	NPC470883
0.7885	Intermediate Similarity	NPC255410
0.7885	Intermediate Similarity	NPC158416
0.7885	Intermediate Similarity	NPC173329
0.7885	Intermediate Similarity	NPC288350
0.7885	Intermediate Similarity	NPC31645
0.7881	Intermediate Similarity	NPC476729
0.7876	Intermediate Similarity	NPC181145
0.787	Intermediate Similarity	NPC100487
0.7864	Intermediate Similarity	NPC256368
0.7864	Intermediate Similarity	NPC469632
0.7857	Intermediate Similarity	NPC302146
0.7857	Intermediate Similarity	NPC70424
0.7857	Intermediate Similarity	NPC11252
0.7857	Intermediate Similarity	NPC289312
0.7857	Intermediate Similarity	NPC243618
0.7857	Intermediate Similarity	NPC9868
0.7851	Intermediate Similarity	NPC213634
0.785	Intermediate Similarity	NPC313569
0.785	Intermediate Similarity	NPC225353
0.7845	Intermediate Similarity	NPC112038
0.7843	Intermediate Similarity	NPC208886
0.7843	Intermediate Similarity	NPC473321
0.7843	Intermediate Similarity	NPC329952
0.7843	Intermediate Similarity	NPC12172
0.7838	Intermediate Similarity	NPC83005
0.783	Intermediate Similarity	NPC475949
0.783	Intermediate Similarity	NPC288876
0.783	Intermediate Similarity	NPC475053
0.783	Intermediate Similarity	NPC472644
0.7826	Intermediate Similarity	NPC474286
0.7826	Intermediate Similarity	NPC475401
0.7826	Intermediate Similarity	NPC13710
0.7826	Intermediate Similarity	NPC475130
0.7818	Intermediate Similarity	NPC219900
0.7818	Intermediate Similarity	NPC475960
0.7818	Intermediate Similarity	NPC392
0.7818	Intermediate Similarity	NPC177524
0.781	Intermediate Similarity	NPC266842
0.7807	Intermediate Similarity	NPC328374
0.7807	Intermediate Similarity	NPC474734
0.7807	Intermediate Similarity	NPC96312
0.7807	Intermediate Similarity	NPC40632
0.7807	Intermediate Similarity	NPC251236
0.7798	Intermediate Similarity	NPC127609

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 NPC472749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1430
0.2-0.3	3566
0.3-0.4	2522
0.4-0.5	904
0.5-0.6	307
0.6-0.7	208
0.7-0.8	52
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.81	Intermediate Similarity	NPD6698	Approved
0.81	Intermediate Similarity	NPD46	Approved
0.8091	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6686	Approved
0.767	Intermediate Similarity	NPD7983	Approved
0.757	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6371	Approved
0.7453	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7838	Discovery
0.7383	Intermediate Similarity	NPD7839	Suspended
0.7358	Intermediate Similarity	NPD5282	Discontinued
0.7333	Intermediate Similarity	NPD8515	Approved
0.7333	Intermediate Similarity	NPD8517	Approved
0.7333	Intermediate Similarity	NPD8513	Phase 3
0.7333	Intermediate Similarity	NPD8516	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7241	Intermediate Similarity	NPD6882	Approved
0.7236	Intermediate Similarity	NPD7507	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7107	Intermediate Similarity	NPD6054	Approved
0.7107	Intermediate Similarity	NPD6319	Approved
0.7103	Intermediate Similarity	NPD5779	Approved
0.7103	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD6616	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.7077	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5785	Approved
0.7073	Intermediate Similarity	NPD8328	Phase 3
0.7063	Intermediate Similarity	NPD7319	Approved
0.7043	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6899	Approved
0.704	Intermediate Similarity	NPD8074	Phase 3
0.704	Intermediate Similarity	NPD7078	Approved
0.7018	Intermediate Similarity	NPD7128	Approved
0.7018	Intermediate Similarity	NPD5739	Approved
0.7018	Intermediate Similarity	NPD6675	Approved
0.7018	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.6992	Remote Similarity	NPD6370	Approved
0.6984	Remote Similarity	NPD7736	Approved
0.6983	Remote Similarity	NPD6373	Approved
0.6983	Remote Similarity	NPD6372	Approved
0.6967	Remote Similarity	NPD6059	Approved
0.6964	Remote Similarity	NPD5344	Discontinued
0.6957	Remote Similarity	NPD5697	Approved
0.6957	Remote Similarity	NPD6412	Phase 2
0.6935	Remote Similarity	NPD7642	Approved
0.6923	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6911	Remote Similarity	NPD6016	Approved
0.6911	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD8293	Discontinued
0.6897	Remote Similarity	NPD7320	Approved
0.6893	Remote Similarity	NPD7154	Phase 3
0.6891	Remote Similarity	NPD4632	Approved
0.6864	Remote Similarity	NPD6847	Approved
0.6864	Remote Similarity	NPD8130	Phase 1
0.6864	Remote Similarity	NPD6617	Approved
0.6864	Remote Similarity	NPD6869	Approved
0.6855	Remote Similarity	NPD5988	Approved
0.6855	Remote Similarity	NPD8080	Discontinued
0.6852	Remote Similarity	NPD6411	Approved
0.6847	Remote Similarity	NPD6083	Phase 2
0.6847	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6012	Approved
0.6838	Remote Similarity	NPD6014	Approved
0.6838	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7260	Phase 2
0.681	Remote Similarity	NPD5701	Approved
0.6807	Remote Similarity	NPD6053	Discontinued
0.6803	Remote Similarity	NPD7641	Discontinued
0.68	Remote Similarity	NPD7830	Approved
0.68	Remote Similarity	NPD7829	Approved
0.6796	Remote Similarity	NPD6435	Approved
0.6774	Remote Similarity	NPD8444	Approved
0.6752	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6110	Phase 1
0.6726	Remote Similarity	NPD7640	Approved
0.6726	Remote Similarity	NPD7639	Approved
0.6721	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5786	Approved
0.6695	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8451	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD8415	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6641	Remote Similarity	NPD8448	Approved
0.664	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7503	Approved
0.664	Remote Similarity	NPD5983	Phase 2
0.6637	Remote Similarity	NPD7638	Approved
0.6636	Remote Similarity	NPD4250	Approved
0.6636	Remote Similarity	NPD4251	Approved
0.6617	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8342	Approved
0.6614	Remote Similarity	NPD8340	Approved
0.6614	Remote Similarity	NPD8341	Approved
0.6614	Remote Similarity	NPD8299	Approved
0.6613	Remote Similarity	NPD7516	Approved
0.6612	Remote Similarity	NPD8133	Approved
0.6609	Remote Similarity	NPD5211	Phase 2
0.6604	Remote Similarity	NPD5363	Approved
0.6604	Remote Similarity	NPD1694	Approved
0.6602	Remote Similarity	NPD4819	Approved
0.6602	Remote Similarity	NPD5368	Approved
0.6602	Remote Similarity	NPD4820	Approved
0.6602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4821	Approved
0.6602	Remote Similarity	NPD4822	Approved
0.6583	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6648	Approved
0.6571	Remote Similarity	NPD5362	Discontinued
0.6562	Remote Similarity	NPD6336	Discontinued
0.656	Remote Similarity	NPD8377	Approved
0.656	Remote Similarity	NPD8294	Approved
0.6545	Remote Similarity	NPD7637	Suspended
0.6542	Remote Similarity	NPD4249	Approved
0.6515	Remote Similarity	NPD6845	Suspended
0.6508	Remote Similarity	NPD6921	Approved
0.6508	Remote Similarity	NPD8296	Approved
0.6508	Remote Similarity	NPD8378	Approved
0.6508	Remote Similarity	NPD8380	Approved
0.6508	Remote Similarity	NPD8335	Approved
0.6508	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4634	Approved
0.6496	Remote Similarity	NPD5141	Approved
0.6491	Remote Similarity	NPD5696	Approved
0.6489	Remote Similarity	NPD8392	Approved
0.6489	Remote Similarity	NPD8391	Approved
0.6489	Remote Similarity	NPD8390	Approved
0.648	Remote Similarity	NPD7100	Approved
0.648	Remote Similarity	NPD7101	Approved
0.6476	Remote Similarity	NPD4270	Approved
0.6476	Remote Similarity	NPD4269	Approved
0.6476	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6033	Approved
0.6446	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5286	Approved
0.6435	Remote Similarity	NPD4696	Approved
0.6435	Remote Similarity	NPD5285	Approved
0.6434	Remote Similarity	NPD8273	Phase 1
0.6422	Remote Similarity	NPD5737	Approved
0.6422	Remote Similarity	NPD6672	Approved
0.6417	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4271	Approved
0.6408	Remote Similarity	NPD4268	Approved
0.6404	Remote Similarity	NPD4755	Approved
0.64	Remote Similarity	NPD6335	Approved
0.6396	Remote Similarity	NPD5693	Phase 1
0.6381	Remote Similarity	NPD5369	Approved
0.6371	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD1695	Approved
0.6339	Remote Similarity	NPD6399	Phase 3
0.633	Remote Similarity	NPD7524	Approved
0.6325	Remote Similarity	NPD5224	Approved
0.6325	Remote Similarity	NPD4633	Approved
0.6325	Remote Similarity	NPD5226	Approved
0.6325	Remote Similarity	NPD5225	Approved
0.632	Remote Similarity	NPD6317	Approved
0.632	Remote Similarity	NPD7500	Approved
0.632	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4756	Discovery
0.6303	Remote Similarity	NPD6008	Approved
0.6299	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4700	Approved
0.6286	Remote Similarity	NPD4252	Approved
0.6275	Remote Similarity	NPD8039	Approved
0.6271	Remote Similarity	NPD5174	Approved
0.6271	Remote Similarity	NPD5175	Approved
0.627	Remote Similarity	NPD6313	Approved
0.627	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5956	Approved
0.624	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.623	Remote Similarity	NPD6421	Discontinued
0.6216	Remote Similarity	NPD4753	Phase 2
0.6216	Remote Similarity	NPD6673	Approved
0.6216	Remote Similarity	NPD6904	Approved
0.6216	Remote Similarity	NPD6080	Approved
0.6204	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4730	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