NPASS Compound

Structure

NPC472995 OpenBabel07101719252D 41 41 0 0 1 0 0 0 0 0999 V2000 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 4.3301 2.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 16 2 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 2 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 21 32 1 0 0 0 0 22 39 1 0 0 0 0 23 33 2 0 0 0 0 23 40 1 0 0 0 0 24 20 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 25 34 1 6 0 0 0 26 27 1 0 0 0 0 26 40 1 6 0 0 0 27 31 1 6 0 0 0 27 35 1 0 0 0 0 28 31 1 6 0 0 0 28 41 1 0 0 0 0 29 36 2 0 0 0 0 29 39 1 0 0 0 0 30 37 2 0 0 0 0 30 41 1 0 0 0 0 31 10 1 6 0 0 0 31 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.31
Volume:	602.986
LogP:	2.348
LogD:	1.268
LogS:	-3.112
# Rotatable Bonds:	15
TPSA:	159.82
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.117
Synthetic Accessibility Score:	5.522
Fsp3:	0.581
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:	-4.775
MDCK Permeability:	3.249424844398163e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.962
Human Intestinal Absorption (HIA):	0.866
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	74.08634185791016%
Volume Distribution (VD):	1.628
Pgp-substrate:	14.638914108276367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.242
CYP2C19-inhibitor:	0.406
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.916
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.114
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	4.168
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.388
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.847
Skin Sensitization:	0.19
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC472995

Natural Product ID:	NPC472995
*Common Name:**	NYAOMORZVGLFQV-NKWFWLRYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NYAOMORZVGLFQV-NKWFWLRYSA-N
Standard InCHI:	InChI=1S/C31H46O10/c1-11-17(6)14-23(33)40-26-24(20(9)22(15-21(32)16(4)5)39-29(36)18(7)12-2)25(34)28(31(10,38)27(26)35)41-30(37)19(8)13-3/h12-14,21-22,24-28,32,34-35,38H,4,9,11,15H2,1-3,5-8,10H3/b17-14+,18-12-,19-13-/t21?,22?,24-,25-,26+,27+,28-,31-/m0/s1
SMILES:	CC/C(=C/C(=O)O[C@@H]1[C@@H](C(=C)C(OC(=O)/C(=CC)/C)CC(C(=C)C)O)[C@H](O)[C@@H]([C@@]([C@@H]1O)(C)O)OC(=O)/C(=CC)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597518
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32699	parasenecio rubescens	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26200396]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	39690.0	nM	PMID[468509]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	71500.0	nM	PMID[468509]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	78900.0	nM	PMID[468509]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.0	mm	PMID[468509]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.0	mm	PMID[468509]

☑ 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 NPC472995 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	193
0.1-0.2	1325
0.2-0.3	4152
0.3-0.4	6351
0.4-0.5	15145
0.5-0.6	9020
0.6-0.7	5315
0.7-0.8	1151
0.8-0.85	32
0.85-0.9	7
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9451	High Similarity	NPC469583
0.9348	High Similarity	NPC472997
0.9348	High Similarity	NPC472996
0.9247	High Similarity	NPC472998
0.8713	High Similarity	NPC475586
0.8673	High Similarity	NPC472552
0.866	High Similarity	NPC272223
0.8571	High Similarity	NPC472554
0.8469	Intermediate Similarity	NPC38855
0.8431	Intermediate Similarity	NPC181994
0.8333	Intermediate Similarity	NPC471205
0.83	Intermediate Similarity	NPC475038
0.83	Intermediate Similarity	NPC109195
0.83	Intermediate Similarity	NPC470972
0.828	Intermediate Similarity	NPC475087
0.8265	Intermediate Similarity	NPC473244
0.8265	Intermediate Similarity	NPC199099
0.8252	Intermediate Similarity	NPC475263
0.8235	Intermediate Similarity	NPC470980
0.8229	Intermediate Similarity	NPC472195
0.8229	Intermediate Similarity	NPC472196
0.8229	Intermediate Similarity	NPC238090
0.8218	Intermediate Similarity	NPC23584
0.8211	Intermediate Similarity	NPC3952
0.8211	Intermediate Similarity	NPC177668
0.82	Intermediate Similarity	NPC11974
0.8172	Intermediate Similarity	NPC311163
0.8163	Intermediate Similarity	NPC471765
0.8163	Intermediate Similarity	NPC284194
0.8163	Intermediate Similarity	NPC221801
0.8163	Intermediate Similarity	NPC211810
0.8155	Intermediate Similarity	NPC67321
0.8155	Intermediate Similarity	NPC122816
0.8155	Intermediate Similarity	NPC473586
0.8155	Intermediate Similarity	NPC187435
0.8144	Intermediate Similarity	NPC159698
0.8119	Intermediate Similarity	NPC11956
0.8105	Intermediate Similarity	NPC133450
0.81	Intermediate Similarity	NPC79303
0.81	Intermediate Similarity	NPC188968
0.8095	Intermediate Similarity	NPC177047
0.809	Intermediate Similarity	NPC477314
0.8081	Intermediate Similarity	NPC120446
0.8077	Intermediate Similarity	NPC50124
0.8077	Intermediate Similarity	NPC38948
0.8065	Intermediate Similarity	NPC471494
0.8061	Intermediate Similarity	NPC276110
0.8061	Intermediate Similarity	NPC36954
0.8061	Intermediate Similarity	NPC476720
0.8058	Intermediate Similarity	NPC88349
0.8058	Intermediate Similarity	NPC51719
0.8058	Intermediate Similarity	NPC111952
0.8056	Intermediate Similarity	NPC154363
0.8056	Intermediate Similarity	NPC471127
0.8056	Intermediate Similarity	NPC234858
0.8039	Intermediate Similarity	NPC474822
0.8	Intermediate Similarity	NPC206618
0.7982	Intermediate Similarity	NPC10721
0.7981	Intermediate Similarity	NPC474716
0.7981	Intermediate Similarity	NPC143609
0.798	Intermediate Similarity	NPC129569
0.7963	Intermediate Similarity	NPC472400
0.7961	Intermediate Similarity	NPC473543
0.7959	Intermediate Similarity	NPC472360
0.7959	Intermediate Similarity	NPC472416
0.7959	Intermediate Similarity	NPC105490
0.7959	Intermediate Similarity	NPC256368
0.7944	Intermediate Similarity	NPC470025
0.7944	Intermediate Similarity	NPC328074
0.7944	Intermediate Similarity	NPC317460
0.7944	Intermediate Similarity	NPC321272
0.7941	Intermediate Similarity	NPC474709
0.7941	Intermediate Similarity	NPC165578
0.7941	Intermediate Similarity	NPC201191
0.7938	Intermediate Similarity	NPC158061
0.7938	Intermediate Similarity	NPC122057
0.7928	Intermediate Similarity	NPC471128
0.7928	Intermediate Similarity	NPC145182
0.7928	Intermediate Similarity	NPC157252
0.7928	Intermediate Similarity	NPC475885
0.7928	Intermediate Similarity	NPC471126
0.7921	Intermediate Similarity	NPC271295
0.7917	Intermediate Similarity	NPC246028
0.7917	Intermediate Similarity	NPC314727
0.7909	Intermediate Similarity	NPC124676
0.7909	Intermediate Similarity	NPC146280
0.7905	Intermediate Similarity	NPC88701
0.7905	Intermediate Similarity	NPC306265
0.79	Intermediate Similarity	NPC254121
0.79	Intermediate Similarity	NPC205143
0.79	Intermediate Similarity	NPC287668
0.79	Intermediate Similarity	NPC40812
0.789	Intermediate Similarity	NPC471816
0.789	Intermediate Similarity	NPC470075
0.7885	Intermediate Similarity	NPC471206
0.787	Intermediate Similarity	NPC472757
0.787	Intermediate Similarity	NPC470027
0.7864	Intermediate Similarity	NPC474124
0.7864	Intermediate Similarity	NPC473523
0.7864	Intermediate Similarity	NPC281378
0.7864	Intermediate Similarity	NPC61442
0.7857	Intermediate Similarity	NPC476300
0.7857	Intermediate Similarity	NPC52839
0.7857	Intermediate Similarity	NPC110022
0.7857	Intermediate Similarity	NPC475912
0.7857	Intermediate Similarity	NPC53555
0.7857	Intermediate Similarity	NPC7349
0.785	Intermediate Similarity	NPC17791
0.785	Intermediate Similarity	NPC470076
0.7849	Intermediate Similarity	NPC44261
0.7843	Intermediate Similarity	NPC475617
0.7838	Intermediate Similarity	NPC156745
0.7838	Intermediate Similarity	NPC236918
0.7835	Intermediate Similarity	NPC312471
0.7835	Intermediate Similarity	NPC474761
0.7835	Intermediate Similarity	NPC476004
0.7835	Intermediate Similarity	NPC473448
0.7835	Intermediate Similarity	NPC471378
0.783	Intermediate Similarity	NPC273433
0.783	Intermediate Similarity	NPC322912
0.7822	Intermediate Similarity	NPC475653
0.7822	Intermediate Similarity	NPC475068
0.7818	Intermediate Similarity	NPC473968
0.7812	Intermediate Similarity	NPC75443
0.7812	Intermediate Similarity	NPC470260
0.7807	Intermediate Similarity	NPC473919
0.7807	Intermediate Similarity	NPC473709
0.7802	Intermediate Similarity	NPC180725
0.7802	Intermediate Similarity	NPC139712
0.78	Intermediate Similarity	NPC165632
0.78	Intermediate Similarity	NPC476315
0.78	Intermediate Similarity	NPC279621
0.78	Intermediate Similarity	NPC475380
0.78	Intermediate Similarity	NPC209297
0.78	Intermediate Similarity	NPC202833
0.7798	Intermediate Similarity	NPC216665
0.7788	Intermediate Similarity	NPC257017
0.7788	Intermediate Similarity	NPC473577
0.7788	Intermediate Similarity	NPC475585
0.7788	Intermediate Similarity	NPC474550
0.7788	Intermediate Similarity	NPC162009
0.7778	Intermediate Similarity	NPC317687
0.7778	Intermediate Similarity	NPC105375
0.7778	Intermediate Similarity	NPC182826
0.7778	Intermediate Similarity	NPC469491
0.7768	Intermediate Similarity	NPC329080
0.7768	Intermediate Similarity	NPC472759
0.7767	Intermediate Similarity	NPC273668
0.7767	Intermediate Similarity	NPC258547
0.7767	Intermediate Similarity	NPC283343
0.7767	Intermediate Similarity	NPC475344
0.7767	Intermediate Similarity	NPC476081
0.7767	Intermediate Similarity	NPC214277
0.7767	Intermediate Similarity	NPC476471
0.7766	Intermediate Similarity	NPC78673
0.7766	Intermediate Similarity	NPC160517
0.7766	Intermediate Similarity	NPC186155
0.7757	Intermediate Similarity	NPC316708
0.7755	Intermediate Similarity	NPC124374
0.7755	Intermediate Similarity	NPC91251
0.7755	Intermediate Similarity	NPC477749
0.7755	Intermediate Similarity	NPC184463
0.7755	Intermediate Similarity	NPC30515
0.7755	Intermediate Similarity	NPC473675
0.7753	Intermediate Similarity	NPC477306
0.7748	Intermediate Similarity	NPC171905
0.7748	Intermediate Similarity	NPC472758
0.7748	Intermediate Similarity	NPC472397
0.7748	Intermediate Similarity	NPC471125
0.7745	Intermediate Similarity	NPC474718
0.7745	Intermediate Similarity	NPC16601
0.7745	Intermediate Similarity	NPC475877
0.7745	Intermediate Similarity	NPC324841
0.7736	Intermediate Similarity	NPC472439
0.7736	Intermediate Similarity	NPC151393
0.7736	Intermediate Similarity	NPC217921
0.7736	Intermediate Similarity	NPC135015
0.7736	Intermediate Similarity	NPC469916
0.7736	Intermediate Similarity	NPC128795
0.7736	Intermediate Similarity	NPC48548
0.7732	Intermediate Similarity	NPC291875
0.7732	Intermediate Similarity	NPC82876
0.7723	Intermediate Similarity	NPC311241
0.7723	Intermediate Similarity	NPC475332
0.7723	Intermediate Similarity	NPC475446
0.7723	Intermediate Similarity	NPC474395
0.7723	Intermediate Similarity	NPC120299
0.7719	Intermediate Similarity	NPC473802
0.7719	Intermediate Similarity	NPC469352
0.7719	Intermediate Similarity	NPC472399
0.7717	Intermediate Similarity	NPC470147
0.7717	Intermediate Similarity	NPC133226
0.7714	Intermediate Similarity	NPC475290
0.7714	Intermediate Similarity	NPC239961
0.7708	Intermediate Similarity	NPC44538
0.7706	Intermediate Similarity	NPC471204
0.7706	Intermediate Similarity	NPC264153
0.7706	Intermediate Similarity	NPC477126
0.77	Intermediate Similarity	NPC14961
0.77	Intermediate Similarity	NPC86893

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 NPC472995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1675
0.2-0.3	3604
0.3-0.4	2342
0.4-0.5	963
0.5-0.6	305
0.6-0.7	81
0.7-0.8	5
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8958	High Similarity	NPD5344	Discontinued
0.8469	Intermediate Similarity	NPD6648	Approved
0.8211	Intermediate Similarity	NPD7838	Discovery
0.8021	Intermediate Similarity	NPD6698	Approved
0.8021	Intermediate Similarity	NPD46	Approved
0.7647	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD7328	Approved
0.7404	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6686	Approved
0.7228	Intermediate Similarity	NPD7983	Approved
0.7156	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6371	Approved
0.7094	Intermediate Similarity	NPD8380	Approved
0.7094	Intermediate Similarity	NPD8379	Approved
0.7094	Intermediate Similarity	NPD8335	Approved
0.7094	Intermediate Similarity	NPD8296	Approved
0.7094	Intermediate Similarity	NPD8033	Approved
0.7094	Intermediate Similarity	NPD8378	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7009	Intermediate Similarity	NPD8294	Approved
0.7009	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7503	Approved
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7507	Approved
0.6832	Remote Similarity	NPD7524	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6807	Remote Similarity	NPD8516	Approved
0.6807	Remote Similarity	NPD8513	Phase 3
0.6807	Remote Similarity	NPD8515	Approved
0.6807	Remote Similarity	NPD8517	Approved
0.6796	Remote Similarity	NPD3168	Discontinued
0.6789	Remote Similarity	NPD7632	Discontinued
0.6739	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6583	Remote Similarity	NPD6319	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD6053	Discontinued
0.6552	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8074	Phase 3
0.6505	Remote Similarity	NPD4250	Approved
0.6505	Remote Similarity	NPD4251	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6486	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4819	Approved
0.6465	Remote Similarity	NPD4820	Approved
0.6465	Remote Similarity	NPD4822	Approved
0.6465	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4821	Approved
0.6436	Remote Similarity	NPD6695	Phase 3
0.6436	Remote Similarity	NPD6110	Phase 1
0.6436	Remote Similarity	NPD7154	Phase 3
0.6435	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4249	Approved
0.6393	Remote Similarity	NPD6921	Approved
0.6374	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8133	Approved
0.6348	Remote Similarity	NPD6881	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD7839	Suspended
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD5785	Approved
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD5357	Phase 1
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6311	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1694	Approved
0.6296	Remote Similarity	NPD7748	Approved
0.6293	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD6373	Approved
0.629	Remote Similarity	NPD8328	Phase 3
0.6273	Remote Similarity	NPD7902	Approved
0.6271	Remote Similarity	NPD6882	Approved
0.6263	Remote Similarity	NPD4271	Approved
0.6263	Remote Similarity	NPD4268	Approved
0.6262	Remote Similarity	NPD7515	Phase 2
0.6261	Remote Similarity	NPD5697	Approved
0.6261	Remote Similarity	NPD6412	Phase 2
0.624	Remote Similarity	NPD7492	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD1695	Approved
0.6207	Remote Similarity	NPD7320	Approved
0.6198	Remote Similarity	NPD7505	Discontinued
0.6198	Remote Similarity	NPD6009	Approved
0.619	Remote Similarity	NPD6616	Approved
0.619	Remote Similarity	NPD7750	Discontinued
0.619	Remote Similarity	NPD8273	Phase 1
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6186	Remote Similarity	NPD6869	Approved
0.6182	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6054	Approved
0.6176	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7604	Phase 2
0.616	Remote Similarity	NPD7642	Approved
0.616	Remote Similarity	NPD7830	Approved
0.616	Remote Similarity	NPD7829	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6142	Remote Similarity	NPD7078	Approved
0.6139	Remote Similarity	NPD6931	Approved
0.6139	Remote Similarity	NPD6930	Phase 2
0.6129	Remote Similarity	NPD5983	Phase 2
0.6121	Remote Similarity	NPD5701	Approved
0.6117	Remote Similarity	NPD5362	Discontinued
0.6115	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6421	Discontinued
0.6094	Remote Similarity	NPD7736	Approved
0.6087	Remote Similarity	NPD371	Approved
0.608	Remote Similarity	NPD6370	Approved
0.6075	Remote Similarity	NPD6101	Approved
0.6075	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6011	Approved
0.6066	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6336	Discontinued
0.6055	Remote Similarity	NPD6399	Phase 3
0.6053	Remote Similarity	NPD5211	Phase 2
0.6048	Remote Similarity	NPD6059	Approved
0.6044	Remote Similarity	NPD368	Approved
0.604	Remote Similarity	NPD6929	Approved
0.6034	Remote Similarity	NPD6008	Approved
0.6016	Remote Similarity	NPD7641	Discontinued
0.6016	Remote Similarity	NPD8293	Discontinued
0.6015	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.5982	Remote Similarity	NPD6083	Phase 2
0.5982	Remote Similarity	NPD6084	Phase 2
0.598	Remote Similarity	NPD7332	Phase 2
0.598	Remote Similarity	NPD7525	Registered
0.598	Remote Similarity	NPD7514	Phase 3
0.597	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD4634	Approved
0.5965	Remote Similarity	NPD4159	Approved
0.5963	Remote Similarity	NPD6411	Approved
0.5963	Remote Similarity	NPD7087	Discontinued
0.5962	Remote Similarity	NPD5331	Approved
0.5962	Remote Similarity	NPD5332	Approved
0.5954	Remote Similarity	NPD7260	Phase 2
0.5952	Remote Similarity	NPD5988	Approved
0.5948	Remote Similarity	NPD5141	Approved
0.5938	Remote Similarity	NPD8451	Approved
0.5935	Remote Similarity	NPD7500	Approved
0.5926	Remote Similarity	NPD6051	Approved
0.5922	Remote Similarity	NPD4790	Discontinued
0.5917	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6640	Phase 3
0.5891	Remote Similarity	NPD8448	Approved
0.5882	Remote Similarity	NPD7645	Phase 2
0.5877	Remote Similarity	NPD5286	Approved
0.5877	Remote Similarity	NPD4696	Approved
0.5877	Remote Similarity	NPD5285	Approved
0.5873	Remote Similarity	NPD8444	Approved
0.5865	Remote Similarity	NPD6435	Approved
0.5865	Remote Similarity	NPD4269	Approved
0.5865	Remote Similarity	NPD4270	Approved
0.5859	Remote Similarity	NPD8341	Approved
0.5859	Remote Similarity	NPD8340	Approved
0.5859	Remote Similarity	NPD8299	Approved
0.5859	Remote Similarity	NPD8342	Approved
0.5854	Remote Similarity	NPD6274	Approved
0.5849	Remote Similarity	NPD6893	Approved
0.5842	Remote Similarity	NPD5776	Phase 2
0.5842	Remote Similarity	NPD6925	Approved
0.5841	Remote Similarity	NPD4755	Approved
0.584	Remote Similarity	NPD7100	Approved
0.584	Remote Similarity	NPD7101	Approved
0.5827	Remote Similarity	NPD7266	Discontinued
0.5821	Remote Similarity	NPD8415	Approved
0.5818	Remote Similarity	NPD6079	Approved
0.5816	Remote Similarity	NPD7625	Phase 1
0.5804	Remote Similarity	NPD5695	Phase 3
0.5794	Remote Similarity	NPD5786	Approved
0.5794	Remote Similarity	NPD3618	Phase 1
0.5784	Remote Similarity	NPD5784	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