NPASS Compound

Structure

NPC131532 OpenBabel07101718302D 47 50 0 0 1 0 0 0 0 0999 V2000 -3.4641 5.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 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 -2.5981 1.5000 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 1.7321 3.0000 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 5.1962 3.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 1.7321 -1.0000 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 -0.0000 3.0000 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 3.4641 3.0000 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 -3.4641 2.0000 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 -0.0000 2.0000 0.0000 C 0 0 1 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 3.4641 -1.0000 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 4.3301 1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 2 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 -3.4641 -0.0000 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 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 0.8660 4.5000 0.0000 O 0 0 0 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -2.5000 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 -3.4641 -1.0000 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 -2.5981 4.5000 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 -0.8660 1.5000 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 1 44 1 0 0 0 0 2 8 1 0 0 0 0 2 19 1 0 0 0 0 3 9 1 0 0 0 0 3 20 1 0 0 0 0 4 10 2 0 0 0 0 4 19 1 0 0 0 0 5 11 2 0 0 0 0 5 20 1 0 0 0 0 6 12 2 0 0 0 0 6 21 1 0 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 31 1 0 0 0 0 14 19 2 0 0 0 0 14 27 1 0 0 0 0 15 20 2 0 0 0 0 15 28 1 0 0 0 0 16 21 2 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 29 1 0 0 0 0 18 45 1 0 0 0 0 22 35 2 0 0 0 0 23 9 1 6 0 0 0 23 46 1 0 0 0 0 24 27 2 0 0 0 0 24 36 1 0 0 0 0 25 28 2 0 0 0 0 25 37 1 0 0 0 0 26 30 2 0 0 0 0 26 38 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 32 1 0 0 0 0 29 41 1 1 0 0 0 30 44 1 0 0 0 0 31 42 2 0 0 0 0 31 47 1 0 0 0 0 32 33 1 0 0 0 0 32 43 1 6 0 0 0 33 34 1 0 0 0 0 33 47 1 1 0 0 0 34 45 1 0 0 0 0 34 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.23
Volume:	645.03
LogP:	2.382
LogD:	1.825
LogS:	-3.472
# Rotatable Bonds:	15
TPSA:	212.67
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.076
Synthetic Accessibility Score:	4.408
Fsp3:	0.353
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.082
MDCK Permeability:	8.526501915184781e-06
Pgp-inhibitor:	0.096
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.845
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.93009185791016%
Volume Distribution (VD):	0.362
Pgp-substrate:	1.8960869312286377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.161
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.409
CYP2D6-substrate:	0.594
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	12.422
Half-life (T1/2):	0.964

ADMET: Toxicity

hERG Blockers:	0.211
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.768
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.97
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.422
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC131532

Natural Product ID:	NPC131532
*Common Name:**	Oregonoyl B
IUPAC Name:	[(2S,3R,4S,5R)-2-[(3S)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy-4,5-dihydroxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	QEQBTRZSJZAYTN-KRKLTZBFSA-N
Standard InCHI:	InChI=1S/C34H38O13/c1-44-30-16-21(6-12-26(30)38)7-13-31(42)47-33-32(43)29(41)18-45-34(33)46-23(9-3-20-5-11-25(37)28(40)15-20)17-22(35)8-2-19-4-10-24(36)27(39)14-19/h4-7,10-16,23,29,32-34,36-41,43H,2-3,8-9,17-18H2,1H3/b13-7+/t23-,29+,32-,33+,34-/m0/s1
SMILES:	COc1cc(/C=C/C(=O)O[C@H]2[C@@H](OC[C@H]([C@@H]2O)O)O[C@H](CC(=O)CCc2ccc(c(c2)O)O)CCc2ccc(c(c2)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590725
PubChem CID:	44602674
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15361	Alnus japonica	Species	Betulaceae	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
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	>	350000.0	nM	PMID[469342]
NPT27	Others	Unspecified		CC50	>	500000.0	nM	PMID[469342]
NPT2	Others	Unspecified		Activity	=	71.3	%	PMID[469343]

☑ 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 NPC131532 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	339
0.1-0.2	1311
0.2-0.3	3012
0.3-0.4	6711
0.4-0.5	10450
0.5-0.6	5779
0.6-0.7	7206
0.7-0.8	6420
0.8-0.85	1249
0.85-0.9	212
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC28776
0.9524	High Similarity	NPC473138
0.92	High Similarity	NPC478242
0.9145	High Similarity	NPC478268
0.9085	High Similarity	NPC87403
0.906	High Similarity	NPC476382
0.906	High Similarity	NPC34587
0.906	High Similarity	NPC252292
0.906	High Similarity	NPC34927
0.906	High Similarity	NPC100998
0.9038	High Similarity	NPC469654
0.902	High Similarity	NPC106818
0.9007	High Similarity	NPC28651
0.9007	High Similarity	NPC199311
0.9007	High Similarity	NPC3460
0.9007	High Similarity	NPC261122
0.9007	High Similarity	NPC80732
0.9007	High Similarity	NPC215095
0.9007	High Similarity	NPC300262
0.9007	High Similarity	NPC116229
0.9007	High Similarity	NPC201148
0.9007	High Similarity	NPC210611
0.9007	High Similarity	NPC192763
0.8987	High Similarity	NPC246024
0.8986	High Similarity	NPC140502
0.8981	High Similarity	NPC44507
0.8974	High Similarity	NPC223335
0.8974	High Similarity	NPC40920
0.8974	High Similarity	NPC133984
0.8954	High Similarity	NPC300329
0.8947	High Similarity	NPC259347
0.8947	High Similarity	NPC306890
0.8947	High Similarity	NPC476398
0.8947	High Similarity	NPC94871
0.8947	High Similarity	NPC470933
0.8947	High Similarity	NPC471062
0.8947	High Similarity	NPC476386
0.8947	High Similarity	NPC473427
0.894	High Similarity	NPC232992
0.891	High Similarity	NPC11411
0.891	High Similarity	NPC471405
0.8896	High Similarity	NPC88560
0.8896	High Similarity	NPC172033
0.8896	High Similarity	NPC175230
0.8889	High Similarity	NPC257970
0.8889	High Similarity	NPC470927
0.8889	High Similarity	NPC188393
0.8889	High Similarity	NPC470934
0.8889	High Similarity	NPC259576
0.8889	High Similarity	NPC221091
0.8854	High Similarity	NPC226759
0.8846	High Similarity	NPC10205
0.8839	High Similarity	NPC299706
0.8839	High Similarity	NPC61604
0.8839	High Similarity	NPC157898
0.8839	High Similarity	NPC115466
0.8839	High Similarity	NPC245615
0.8831	High Similarity	NPC7145
0.8831	High Similarity	NPC143480
0.8831	High Similarity	NPC125823
0.8831	High Similarity	NPC85192
0.8824	High Similarity	NPC111785
0.8808	High Similarity	NPC262182
0.8808	High Similarity	NPC287615
0.8808	High Similarity	NPC216819
0.8808	High Similarity	NPC83743
0.88	High Similarity	NPC478239
0.8797	High Similarity	NPC469384
0.8797	High Similarity	NPC478269
0.8795	High Similarity	NPC471030
0.879	High Similarity	NPC478055
0.8782	High Similarity	NPC327032
0.8782	High Similarity	NPC191046
0.8782	High Similarity	NPC194095
0.878	High Similarity	NPC316539
0.878	High Similarity	NPC472993
0.8774	High Similarity	NPC289967
0.8774	High Similarity	NPC472611
0.8774	High Similarity	NPC472612
0.8773	High Similarity	NPC204937
0.8773	High Similarity	NPC149011
0.8766	High Similarity	NPC476871
0.8765	High Similarity	NPC128403
0.8758	High Similarity	NPC1580
0.875	High Similarity	NPC285108
0.875	High Similarity	NPC33298
0.875	High Similarity	NPC476865
0.8742	High Similarity	NPC110063
0.8735	High Similarity	NPC267549
0.8734	High Similarity	NPC472860
0.8734	High Similarity	NPC286919
0.8734	High Similarity	NPC475663
0.8733	High Similarity	NPC157816
0.8726	High Similarity	NPC38699
0.872	High Similarity	NPC47140
0.872	High Similarity	NPC67134
0.8718	High Similarity	NPC137813
0.8718	High Similarity	NPC44730
0.8712	High Similarity	NPC197708
0.8712	High Similarity	NPC21956
0.8712	High Similarity	NPC658
0.8707	High Similarity	NPC103398
0.8707	High Similarity	NPC180171
0.8707	High Similarity	NPC158325
0.8701	High Similarity	NPC106138
0.8696	High Similarity	NPC227297
0.8696	High Similarity	NPC121290
0.869	High Similarity	NPC199172
0.869	High Similarity	NPC35924
0.8688	High Similarity	NPC149873
0.8688	High Similarity	NPC7191
0.8688	High Similarity	NPC478267
0.8684	High Similarity	NPC143120
0.8684	High Similarity	NPC274960
0.8684	High Similarity	NPC473909
0.8684	High Similarity	NPC476868
0.8684	High Similarity	NPC476866
0.8684	High Similarity	NPC476864
0.8684	High Similarity	NPC476869
0.8679	High Similarity	NPC179914
0.8675	High Similarity	NPC79736
0.8675	High Similarity	NPC67629
0.8671	High Similarity	NPC470896
0.8671	High Similarity	NPC473275
0.8671	High Similarity	NPC163635
0.8667	High Similarity	NPC476377
0.8667	High Similarity	NPC134405
0.8667	High Similarity	NPC47471
0.8667	High Similarity	NPC476385
0.8667	High Similarity	NPC186406
0.8662	High Similarity	NPC469888
0.8658	High Similarity	NPC197316
0.8658	High Similarity	NPC81515
0.8658	High Similarity	NPC472350
0.8658	High Similarity	NPC89105
0.8658	High Similarity	NPC64141
0.8658	High Similarity	NPC68092
0.8658	High Similarity	NPC476383
0.8654	High Similarity	NPC36130
0.8654	High Similarity	NPC134905
0.865	High Similarity	NPC116745
0.865	High Similarity	NPC229729
0.865	High Similarity	NPC298847
0.8649	High Similarity	NPC52277
0.8649	High Similarity	NPC177035
0.8649	High Similarity	NPC199459
0.8649	High Similarity	NPC157554
0.8645	High Similarity	NPC12006
0.8645	High Similarity	NPC158635
0.8645	High Similarity	NPC229882
0.8642	High Similarity	NPC475738
0.8639	High Similarity	NPC25946
0.8639	High Similarity	NPC470720
0.8639	High Similarity	NPC470717
0.8639	High Similarity	NPC460984
0.8639	High Similarity	NPC470713
0.8639	High Similarity	NPC21359
0.8639	High Similarity	NPC471110
0.8634	High Similarity	NPC148273
0.8634	High Similarity	NPC471873
0.8631	High Similarity	NPC469371
0.8627	High Similarity	NPC199928
0.8625	High Similarity	NPC239966
0.8625	High Similarity	NPC203020
0.8625	High Similarity	NPC289346
0.8623	High Similarity	NPC476619
0.8623	High Similarity	NPC476618
0.8623	High Similarity	NPC476621
0.8623	High Similarity	NPC139571
0.8623	High Similarity	NPC217520
0.8623	High Similarity	NPC476620
0.8623	High Similarity	NPC476622
0.8623	High Similarity	NPC472387
0.8623	High Similarity	NPC477895
0.8623	High Similarity	NPC476623
0.8618	High Similarity	NPC232228
0.8618	High Similarity	NPC476867
0.8616	High Similarity	NPC471878
0.8614	High Similarity	NPC473630
0.8609	High Similarity	NPC265648
0.8609	High Similarity	NPC222433
0.8606	High Similarity	NPC469777
0.8606	High Similarity	NPC469772
0.8606	High Similarity	NPC469773
0.8606	High Similarity	NPC102851
0.8606	High Similarity	NPC100925
0.8606	High Similarity	NPC469775
0.8606	High Similarity	NPC469778
0.8606	High Similarity	NPC32723
0.8606	High Similarity	NPC135334
0.8606	High Similarity	NPC469776
0.8606	High Similarity	NPC5786
0.8606	High Similarity	NPC295941
0.8606	High Similarity	NPC469774
0.86	High Similarity	NPC473799
0.86	High Similarity	NPC475530
0.8598	High Similarity	NPC229687
0.8591	High Similarity	NPC78363
0.8591	High Similarity	NPC260425
0.859	High Similarity	NPC243891

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 NPC131532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	822
0.2-0.3	1596
0.3-0.4	2586
0.4-0.5	2065
0.5-0.6	1106
0.6-0.7	558
0.7-0.8	108
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8658	High Similarity	NPD7266	Discontinued
0.8545	High Similarity	NPD7074	Phase 3
0.8485	Intermediate Similarity	NPD7054	Approved
0.8434	Intermediate Similarity	NPD7472	Approved
0.8333	Intermediate Similarity	NPD7685	Pre-registration
0.8323	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7228	Approved
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8284	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7808	Phase 3
0.8246	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7251	Discontinued
0.821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8166	Intermediate Similarity	NPD6797	Phase 2
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD8312	Approved
0.8129	Intermediate Similarity	NPD8313	Approved
0.811	Intermediate Similarity	NPD6234	Discontinued
0.8086	Intermediate Similarity	NPD8455	Phase 2
0.805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1934	Approved
0.8025	Intermediate Similarity	NPD37	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD1653	Approved
0.7988	Intermediate Similarity	NPD4967	Phase 2
0.7988	Intermediate Similarity	NPD4966	Approved
0.7988	Intermediate Similarity	NPD4965	Approved
0.7962	Intermediate Similarity	NPD6190	Approved
0.7953	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7240	Approved
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD4380	Phase 2
0.7785	Intermediate Similarity	NPD8166	Discontinued
0.777	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5844	Phase 1
0.7725	Intermediate Similarity	NPD7075	Discontinued
0.7719	Intermediate Similarity	NPD7473	Discontinued
0.7711	Intermediate Similarity	NPD3817	Phase 2
0.7697	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD8127	Discontinued
0.7651	Intermediate Similarity	NPD2801	Approved
0.7647	Intermediate Similarity	NPD6232	Discontinued
0.761	Intermediate Similarity	NPD6674	Discontinued
0.7602	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6233	Phase 2
0.7581	Intermediate Similarity	NPD7680	Approved
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.756	Intermediate Similarity	NPD3882	Suspended
0.7545	Intermediate Similarity	NPD7819	Suspended
0.7545	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7532	Intermediate Similarity	NPD6798	Discontinued
0.753	Intermediate Similarity	NPD7411	Suspended
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7459	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7768	Phase 2
0.744	Intermediate Similarity	NPD1465	Phase 2
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1511	Approved
0.7405	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD5403	Approved
0.7394	Intermediate Similarity	NPD7435	Discontinued
0.7391	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6801	Discontinued
0.7356	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD1512	Approved
0.7326	Intermediate Similarity	NPD5494	Approved
0.7297	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD447	Suspended
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5401	Approved
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.7262	Intermediate Similarity	NPD7028	Phase 2
0.7254	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7874	Approved
0.7249	Intermediate Similarity	NPD6823	Phase 2
0.7244	Intermediate Similarity	NPD7095	Approved
0.7239	Intermediate Similarity	NPD4110	Phase 3
0.7239	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7226	Intermediate Similarity	NPD9494	Approved
0.7222	Intermediate Similarity	NPD1549	Phase 2
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6799	Approved
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7697	Approved
0.7207	Intermediate Similarity	NPD7039	Approved
0.7207	Intermediate Similarity	NPD7038	Approved
0.7202	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7184	Intermediate Similarity	NPD6959	Discontinued
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7134	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD6273	Approved
0.7118	Intermediate Similarity	NPD6386	Approved
0.7118	Intermediate Similarity	NPD6385	Approved
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD3455	Phase 2
0.7101	Intermediate Similarity	NPD3226	Approved
0.7089	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3764	Approved
0.7086	Intermediate Similarity	NPD1357	Approved
0.7083	Intermediate Similarity	NPD8319	Approved
0.7083	Intermediate Similarity	NPD8320	Phase 1
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7066	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3705	Approved
0.7059	Intermediate Similarity	NPD1091	Approved
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD2346	Discontinued
0.7051	Intermediate Similarity	NPD2798	Approved
0.7044	Intermediate Similarity	NPD4062	Phase 3
0.7041	Intermediate Similarity	NPD7801	Approved
0.7037	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD7700	Phase 2
0.7037	Intermediate Similarity	NPD7699	Phase 2
0.703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6653	Approved
0.7011	Intermediate Similarity	NPD3749	Approved
0.7007	Intermediate Similarity	NPD228	Approved
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD3620	Phase 2
0.6994	Remote Similarity	NPD2438	Suspended
0.6994	Remote Similarity	NPD2796	Approved
0.6987	Remote Similarity	NPD2797	Approved
0.6984	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3268	Approved
0.6981	Remote Similarity	NPD2313	Discontinued
0.698	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6534	Approved
0.6968	Remote Similarity	NPD6535	Approved
0.6964	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4908	Phase 1
0.6946	Remote Similarity	NPD7440	Discontinued
0.6943	Remote Similarity	NPD5647	Approved
0.6928	Remote Similarity	NPD7003	Approved
0.6923	Remote Similarity	NPD7584	Approved
0.6915	Remote Similarity	NPD6212	Phase 3
0.6915	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6213	Phase 3
0.6914	Remote Similarity	NPD1607	Approved
0.6913	Remote Similarity	NPD5283	Phase 1
0.6909	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1608	Approved
0.6897	Remote Similarity	NPD5353	Approved
0.6894	Remote Similarity	NPD943	Approved
0.6894	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1551	Phase 2
0.6885	Remote Similarity	NPD7549	Discontinued
0.6879	Remote Similarity	NPD6844	Discontinued
0.6879	Remote Similarity	NPD1203	Approved
0.6875	Remote Similarity	NPD919	Approved
0.6875	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7930	Approved
0.6846	Remote Similarity	NPD7843	Approved
0.6845	Remote Similarity	NPD5058	Phase 3
0.6839	Remote Similarity	NPD2977	Approved
0.6839	Remote Similarity	NPD1535	Discovery
0.6839	Remote Similarity	NPD2978	Approved
0.6839	Remote Similarity	NPD1547	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