NPASS Compound

Structure

NPC469527 OpenBabel07101718302D 30 32 0 0 1 0 0 0 0 0999 V2000 1.7321 -4.0000 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 0.8660 -4.5000 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 -2.5000 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 -0.8660 -2.5000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 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 5.1962 -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 2 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 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 3.4641 0.0000 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 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 11 1 0 0 0 0 8 27 1 0 0 0 0 9 12 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 6 0 0 0 13 10 1 1 0 0 0 13 15 1 0 0 0 0 13 30 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 23 1 6 0 0 0 16 18 1 0 0 0 0 16 24 1 1 0 0 0 17 19 1 0 0 0 0 17 25 1 1 0 0 0 18 20 1 0 0 0 0 18 26 1 6 0 0 0 19 28 1 0 0 0 0 19 29 1 6 0 0 0 20 27 1 6 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.17
Volume:	406.163
LogP:	-0.436
LogD:	-0.147
LogS:	-1.671
# Rotatable Bonds:	7
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.286
Synthetic Accessibility Score:	4.291
Fsp3:	0.6
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:	-5.399
MDCK Permeability:	1.3243727153167129e-05
Pgp-inhibitor:	0.573
Pgp-substrate:	0.829
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.354
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	59.803436279296875%
Volume Distribution (VD):	0.486
Pgp-substrate:	25.37444496154785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	1.08
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.52
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.921
Carcinogencity:	0.201
Eye Corrosion:	0.005
Eye Irritation:	0.502
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC469527

Natural Product ID:	NPC469527
*Common Name:**	Rosavin
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[(E)-3-phenylprop-2-enoxy]-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:	Rosavin
Standard InCHIKey:	RINHYCZCUGCZAJ-UHAHJPEESA-N
Standard InCHI:	InChI=1S/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20-/m0/s1
SMILES:	O[C@@H]1[C@@H](O)[C@@H](OC/C=C/c2ccccc2)O[C@@H]([C@H]1O)CO[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1083511
PubChem CID:	6440755
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	10000000.0	nM	PMID[520989]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	18.7	%	PMID[520990]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[520990]

☑ 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 NPC469527 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	240
0.1-0.2	1082
0.2-0.3	2982
0.3-0.4	9143
0.4-0.5	15775
0.5-0.6	10916
0.6-0.7	2191
0.7-0.8	339
0.8-0.85	13
0.85-0.9	10
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9406	High Similarity	NPC474148
0.9406	High Similarity	NPC276061
0.9314	High Similarity	NPC30563
0.9223	High Similarity	NPC470825
0.9118	High Similarity	NPC184633
0.901	High Similarity	NPC37714
0.901	High Similarity	NPC152384
0.8942	High Similarity	NPC264784
0.8868	High Similarity	NPC474641
0.8788	High Similarity	NPC262826
0.8762	High Similarity	NPC43584
0.8725	High Similarity	NPC47286
0.8716	High Similarity	NPC122245
0.8716	High Similarity	NPC266389
0.8716	High Similarity	NPC216605
0.8611	High Similarity	NPC29607
0.8544	High Similarity	NPC148060
0.8349	Intermediate Similarity	NPC120217
0.8273	Intermediate Similarity	NPC313193
0.8261	Intermediate Similarity	NPC140561
0.8261	Intermediate Similarity	NPC141970
0.8246	Intermediate Similarity	NPC229600
0.8125	Intermediate Similarity	NPC175771
0.812	Intermediate Similarity	NPC162925
0.812	Intermediate Similarity	NPC87153
0.812	Intermediate Similarity	NPC57607
0.8103	Intermediate Similarity	NPC476142
0.8051	Intermediate Similarity	NPC77651
0.8051	Intermediate Similarity	NPC28069
0.8017	Intermediate Similarity	NPC55608
0.7983	Intermediate Similarity	NPC290276
0.7983	Intermediate Similarity	NPC114096
0.7983	Intermediate Similarity	NPC63404
0.7983	Intermediate Similarity	NPC198918
0.7983	Intermediate Similarity	NPC10121
0.7983	Intermediate Similarity	NPC231888
0.7983	Intermediate Similarity	NPC92283
0.7983	Intermediate Similarity	NPC204214
0.7983	Intermediate Similarity	NPC124878
0.7983	Intermediate Similarity	NPC35338
0.7983	Intermediate Similarity	NPC10883
0.7966	Intermediate Similarity	NPC145287
0.7965	Intermediate Similarity	NPC148055
0.7949	Intermediate Similarity	NPC52097
0.7946	Intermediate Similarity	NPC157338
0.7931	Intermediate Similarity	NPC469703
0.7931	Intermediate Similarity	NPC469412
0.7931	Intermediate Similarity	NPC469704
0.7931	Intermediate Similarity	NPC160854
0.7931	Intermediate Similarity	NPC201402
0.7931	Intermediate Similarity	NPC198734
0.7917	Intermediate Similarity	NPC148026
0.7917	Intermediate Similarity	NPC231627
0.7917	Intermediate Similarity	NPC471025
0.7917	Intermediate Similarity	NPC106677
0.7913	Intermediate Similarity	NPC14950
0.7899	Intermediate Similarity	NPC83218
0.7899	Intermediate Similarity	NPC126991
0.7863	Intermediate Similarity	NPC469686
0.7863	Intermediate Similarity	NPC11724
0.7851	Intermediate Similarity	NPC237182
0.7851	Intermediate Similarity	NPC226101
0.7851	Intermediate Similarity	NPC471024
0.7845	Intermediate Similarity	NPC282409
0.7845	Intermediate Similarity	NPC469708
0.7845	Intermediate Similarity	NPC469702
0.7845	Intermediate Similarity	NPC60589
0.7833	Intermediate Similarity	NPC471157
0.7833	Intermediate Similarity	NPC267733
0.7833	Intermediate Similarity	NPC276047
0.7833	Intermediate Similarity	NPC252114
0.7815	Intermediate Similarity	NPC287429
0.7797	Intermediate Similarity	NPC471067
0.7778	Intermediate Similarity	NPC476445
0.7778	Intermediate Similarity	NPC476448
0.7778	Intermediate Similarity	NPC269242
0.7778	Intermediate Similarity	NPC476872
0.7778	Intermediate Similarity	NPC469548
0.7769	Intermediate Similarity	NPC288416
0.7769	Intermediate Similarity	NPC175333
0.7759	Intermediate Similarity	NPC476096
0.775	Intermediate Similarity	NPC470510
0.7731	Intermediate Similarity	NPC178449
0.7731	Intermediate Similarity	NPC232454
0.7731	Intermediate Similarity	NPC470907
0.7724	Intermediate Similarity	NPC319995
0.7724	Intermediate Similarity	NPC289415
0.7712	Intermediate Similarity	NPC226712
0.7705	Intermediate Similarity	NPC301857
0.7705	Intermediate Similarity	NPC225307
0.7686	Intermediate Similarity	NPC147032
0.7667	Intermediate Similarity	NPC244454
0.7661	Intermediate Similarity	NPC138777
0.7661	Intermediate Similarity	NPC225384
0.7661	Intermediate Similarity	NPC9912
0.7661	Intermediate Similarity	NPC246869
0.7661	Intermediate Similarity	NPC46137
0.7661	Intermediate Similarity	NPC235294
0.7642	Intermediate Similarity	NPC253595
0.7642	Intermediate Similarity	NPC295970
0.7623	Intermediate Similarity	NPC471882
0.7623	Intermediate Similarity	NPC45224
0.7623	Intermediate Similarity	NPC35288
0.7623	Intermediate Similarity	NPC156692
0.7623	Intermediate Similarity	NPC173150
0.7623	Intermediate Similarity	NPC471881
0.76	Intermediate Similarity	NPC473285
0.76	Intermediate Similarity	NPC254275
0.7583	Intermediate Similarity	NPC212176
0.7581	Intermediate Similarity	NPC17567
0.7563	Intermediate Similarity	NPC266045
0.7561	Intermediate Similarity	NPC302378
0.7521	Intermediate Similarity	NPC228907
0.752	Intermediate Similarity	NPC254819
0.752	Intermediate Similarity	NPC475067
0.752	Intermediate Similarity	NPC478255
0.75	Intermediate Similarity	NPC301651
0.75	Intermediate Similarity	NPC27712
0.75	Intermediate Similarity	NPC248355
0.75	Intermediate Similarity	NPC477294
0.75	Intermediate Similarity	NPC473556
0.75	Intermediate Similarity	NPC477293
0.75	Intermediate Similarity	NPC307110
0.75	Intermediate Similarity	NPC229784
0.75	Intermediate Similarity	NPC184092
0.75	Intermediate Similarity	NPC218003
0.748	Intermediate Similarity	NPC231607
0.748	Intermediate Similarity	NPC188555
0.748	Intermediate Similarity	NPC108659
0.748	Intermediate Similarity	NPC87696
0.748	Intermediate Similarity	NPC264900
0.748	Intermediate Similarity	NPC130496
0.748	Intermediate Similarity	NPC469687
0.748	Intermediate Similarity	NPC79715
0.748	Intermediate Similarity	NPC35731
0.746	Intermediate Similarity	NPC26080
0.746	Intermediate Similarity	NPC303422
0.746	Intermediate Similarity	NPC165686
0.746	Intermediate Similarity	NPC85799
0.7459	Intermediate Similarity	NPC90318
0.744	Intermediate Similarity	NPC80600
0.744	Intermediate Similarity	NPC472024
0.7438	Intermediate Similarity	NPC138798
0.7438	Intermediate Similarity	NPC473881
0.7422	Intermediate Similarity	NPC470236
0.7422	Intermediate Similarity	NPC263829
0.7422	Intermediate Similarity	NPC238243
0.7419	Intermediate Similarity	NPC40377
0.7419	Intermediate Similarity	NPC232880
0.7419	Intermediate Similarity	NPC146540
0.7419	Intermediate Similarity	NPC148982
0.7402	Intermediate Similarity	NPC28637
0.7402	Intermediate Similarity	NPC322503
0.7402	Intermediate Similarity	NPC294166
0.7402	Intermediate Similarity	NPC115022
0.7402	Intermediate Similarity	NPC470143
0.7398	Intermediate Similarity	NPC61181
0.7398	Intermediate Similarity	NPC94179
0.7398	Intermediate Similarity	NPC471026
0.7381	Intermediate Similarity	NPC65942
0.7381	Intermediate Similarity	NPC219677
0.7381	Intermediate Similarity	NPC248307
0.7381	Intermediate Similarity	NPC121376
0.7381	Intermediate Similarity	NPC281798
0.7368	Intermediate Similarity	NPC234376
0.7364	Intermediate Similarity	NPC3293
0.7364	Intermediate Similarity	NPC164857
0.7364	Intermediate Similarity	NPC197723
0.7364	Intermediate Similarity	NPC165482
0.7364	Intermediate Similarity	NPC469383
0.7364	Intermediate Similarity	NPC472132
0.7364	Intermediate Similarity	NPC138350
0.7364	Intermediate Similarity	NPC40664
0.736	Intermediate Similarity	NPC97326
0.736	Intermediate Similarity	NPC270849
0.736	Intermediate Similarity	NPC11025
0.736	Intermediate Similarity	NPC26653
0.736	Intermediate Similarity	NPC166040
0.7344	Intermediate Similarity	NPC187194
0.7344	Intermediate Similarity	NPC287597
0.7344	Intermediate Similarity	NPC169398
0.7344	Intermediate Similarity	NPC476411
0.7344	Intermediate Similarity	NPC886
0.7344	Intermediate Similarity	NPC34293
0.7339	Intermediate Similarity	NPC103533
0.7339	Intermediate Similarity	NPC198798
0.7339	Intermediate Similarity	NPC476873
0.7323	Intermediate Similarity	NPC162093
0.7323	Intermediate Similarity	NPC473924
0.7323	Intermediate Similarity	NPC252833
0.7317	Intermediate Similarity	NPC12308
0.7317	Intermediate Similarity	NPC123704
0.7308	Intermediate Similarity	NPC65262
0.7308	Intermediate Similarity	NPC476376
0.7308	Intermediate Similarity	NPC260425
0.7308	Intermediate Similarity	NPC78363
0.7308	Intermediate Similarity	NPC469364
0.7308	Intermediate Similarity	NPC262328
0.7308	Intermediate Similarity	NPC87777
0.7308	Intermediate Similarity	NPC304152

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 NPC469527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	729
0.2-0.3	1563
0.3-0.4	3500
0.4-0.5	2248
0.5-0.6	851
0.6-0.7	53
0.7-0.8	4
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
0.7845	Intermediate Similarity	NPD5126	Approved
0.7845	Intermediate Similarity	NPD5125	Phase 3
0.7712	Intermediate Similarity	NPD1091	Approved
0.7368	Intermediate Similarity	NPD969	Suspended
0.7252	Intermediate Similarity	NPD7266	Discontinued
0.7054	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5048	Discontinued
0.6952	Remote Similarity	NPD689	Discontinued
0.6884	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD7741	Discontinued
0.6638	Remote Similarity	NPD6685	Approved
0.6604	Remote Similarity	NPD1282	Approved
0.6581	Remote Similarity	NPD290	Approved
0.6557	Remote Similarity	NPD4198	Discontinued
0.6549	Remote Similarity	NPD7798	Approved
0.6522	Remote Similarity	NPD5765	Approved
0.6522	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6647	Phase 2
0.6519	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8455	Phase 2
0.6503	Remote Similarity	NPD1653	Approved
0.65	Remote Similarity	NPD5058	Phase 3
0.65	Remote Similarity	NPD6912	Phase 3
0.6484	Remote Similarity	NPD7876	Discontinued
0.6466	Remote Similarity	NPD4404	Approved
0.6446	Remote Similarity	NPD7843	Approved
0.6441	Remote Similarity	NPD9532	Phase 3
0.6436	Remote Similarity	NPD9294	Approved
0.6403	Remote Similarity	NPD6674	Discontinued
0.6389	Remote Similarity	NPD531	Approved
0.6387	Remote Similarity	NPD2684	Approved
0.6371	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD1357	Approved
0.6341	Remote Similarity	NPD2629	Approved
0.6333	Remote Similarity	NPD2067	Discontinued
0.6328	Remote Similarity	NPD3705	Approved
0.6316	Remote Similarity	NPD9495	Approved
0.6316	Remote Similarity	NPD3027	Phase 3
0.6299	Remote Similarity	NPD5723	Approved
0.6296	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1613	Approved
0.629	Remote Similarity	NPD7157	Approved
0.6277	Remote Similarity	NPD41	Approved
0.6277	Remote Similarity	NPD5886	Approved
0.6277	Remote Similarity	NPD4538	Approved
0.6277	Remote Similarity	NPD4536	Approved
0.6277	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD5588	Approved
0.6232	Remote Similarity	NPD5960	Phase 3
0.6197	Remote Similarity	NPD6190	Approved
0.6186	Remote Similarity	NPD5909	Discontinued
0.6174	Remote Similarity	NPD5926	Approved
0.617	Remote Similarity	NPD1652	Phase 2
0.6167	Remote Similarity	NPD6406	Approved
0.6159	Remote Similarity	NPD7097	Phase 1
0.6129	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6233	Phase 2
0.609	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD3526	Approved
0.6083	Remote Similarity	NPD968	Approved
0.6083	Remote Similarity	NPD3524	Approved
0.6074	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD2558	Approved
0.6068	Remote Similarity	NPD2553	Approved
0.6068	Remote Similarity	NPD2555	Approved
0.6068	Remote Similarity	NPD2550	Approved
0.6068	Remote Similarity	NPD2552	Approved
0.6068	Remote Similarity	NPD2549	Approved
0.6066	Remote Similarity	NPD9713	Approved
0.6061	Remote Similarity	NPD8651	Approved
0.6056	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6516	Phase 2
0.6047	Remote Similarity	NPD5846	Approved
0.6045	Remote Similarity	NPD2861	Phase 2
0.6034	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD1358	Approved
0.6017	Remote Similarity	NPD291	Approved
0.6017	Remote Similarity	NPD4189	Approved
0.6017	Remote Similarity	NPD4188	Approved
0.6016	Remote Similarity	NPD1548	Phase 1
0.6013	Remote Similarity	NPD7054	Approved
0.6013	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4908	Phase 1
0.6	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6	Remote Similarity	NPD794	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD3685	Discontinued
0.5984	Remote Similarity	NPD5291	Approved
0.5984	Remote Similarity	NPD5292	Approved
0.5975	Remote Similarity	NPD7074	Phase 3
0.5975	Remote Similarity	NPD7472	Approved
0.5972	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD3718	Approved
0.5965	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD3719	Approved
0.5956	Remote Similarity	NPD3179	Approved
0.5956	Remote Similarity	NPD3180	Approved
0.5954	Remote Similarity	NPD1610	Phase 2
0.5949	Remote Similarity	NPD7228	Approved
0.5938	Remote Similarity	NPD6797	Phase 2
0.5935	Remote Similarity	NPD556	Approved
0.5931	Remote Similarity	NPD3122	Phase 3
0.5929	Remote Similarity	NPD9365	Approved
0.5926	Remote Similarity	NPD3971	Phase 1
0.5926	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD9716	Approved
0.5917	Remote Similarity	NPD3046	Approved
0.5917	Remote Similarity	NPD3047	Approved
0.5917	Remote Similarity	NPD3048	Approved
0.5913	Remote Similarity	NPD2934	Approved
0.5913	Remote Similarity	NPD2933	Approved
0.5912	Remote Similarity	NPD6798	Discontinued
0.5912	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7508	Discontinued
0.5903	Remote Similarity	NPD2575	Approved
0.5902	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6686	Approved
0.5901	Remote Similarity	NPD7251	Discontinued
0.5899	Remote Similarity	NPD4340	Discontinued
0.5899	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD5124	Phase 1
0.5896	Remote Similarity	NPD2159	Approved
0.5896	Remote Similarity	NPD2625	Approved
0.5896	Remote Similarity	NPD2627	Approved
0.5896	Remote Similarity	NPD3094	Phase 2
0.5896	Remote Similarity	NPD2160	Approved
0.5896	Remote Similarity	NPD2628	Approved
0.5896	Remote Similarity	NPD2626	Approved
0.5894	Remote Similarity	NPD37	Approved
0.5888	Remote Similarity	NPD226	Approved
0.5887	Remote Similarity	NPD7033	Discontinued
0.5887	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD4108	Discontinued
0.5882	Remote Similarity	NPD4967	Phase 2
0.5882	Remote Similarity	NPD4966	Approved
0.5882	Remote Similarity	NPD2613	Approved
0.5882	Remote Similarity	NPD4965	Approved
0.5867	Remote Similarity	NPD4380	Phase 2
0.5865	Remote Similarity	NPD2982	Phase 2
0.5865	Remote Similarity	NPD2983	Phase 2
0.5864	Remote Similarity	NPD7808	Phase 3
0.5862	Remote Similarity	NPD2860	Approved
0.5862	Remote Similarity	NPD2859	Approved
0.5857	Remote Similarity	NPD6653	Approved
0.5856	Remote Similarity	NPD4793	Discontinued
0.5854	Remote Similarity	NPD2182	Approved
0.5852	Remote Similarity	NPD7247	Discontinued
0.5849	Remote Similarity	NPD3818	Discontinued
0.5847	Remote Similarity	NPD1238	Approved
0.5841	Remote Similarity	NPD3673	Approved
0.5841	Remote Similarity	NPD3672	Approved
0.584	Remote Similarity	NPD4573	Approved
0.584	Remote Similarity	NPD4572	Approved
0.584	Remote Similarity	NPD4571	Approved
0.5833	Remote Similarity	NPD744	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD8313	Approved
0.5828	Remote Similarity	NPD8312	Approved
0.5822	Remote Similarity	NPD5756	Phase 2
0.582	Remote Similarity	NPD2551	Approved
0.582	Remote Similarity	NPD3134	Approved
0.582	Remote Similarity	NPD811	Approved
0.582	Remote Similarity	NPD2559	Approved
0.582	Remote Similarity	NPD812	Approved
0.582	Remote Similarity	NPD810	Approved
0.5806	Remote Similarity	NPD6234	Discontinued
0.5804	Remote Similarity	NPD521	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5763	Approved
0.5804	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5762	Approved
0.5802	Remote Similarity	NPD5305	Approved
0.5802	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7685	Pre-registration
0.5802	Remote Similarity	NPD7240	Approved
0.5802	Remote Similarity	NPD5306	Approved
0.5802	Remote Similarity	NPD6559	Discontinued
0.5798	Remote Similarity	NPD1242	Phase 1
0.5797	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5796	Remote Similarity	NPD3787	Discontinued
0.5794	Remote Similarity	NPD1138	Approved
0.5793	Remote Similarity	NPD4535	Phase 3
0.5793	Remote Similarity	NPD4628	Phase 3
0.5789	Remote Similarity	NPD2981	Phase 2
0.5789	Remote Similarity	NPD7249	Approved
0.5789	Remote Similarity	NPD7250	Approved
0.5789	Remote Similarity	NPD2235	Phase 2
0.5789	Remote Similarity	NPD2231	Phase 2
0.5785	Remote Similarity	NPD1237	Approved
0.5782	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6671	Approved
0.578	Remote Similarity	NPD9491	Approved
0.5776	Remote Similarity	NPD4814	Discontinued
0.5772	Remote Similarity	NPD5403	Approved
0.5769	Remote Similarity	NPD9545	Approved
0.5767	Remote Similarity	NPD4338	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