NPASS Compound

Structure

NPC113295 OpenBabel07101719512D 28 29 0 0 1 0 0 0 0 0999 V2000 6.9282 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 3.4641 -0.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 0.8660 -2.5000 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 3.4641 -1.0000 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 1.7321 -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 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 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 2.5981 -2.5000 0.0000 C 0 0 2 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 O 0 0 0 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 12 18 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 19 13 1 6 0 0 0 19 20 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.15
Volume:	389.23
LogP:	0.935
LogD:	1.42
LogS:	-2.616
# Rotatable Bonds:	9
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	3.222
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.878
MDCK Permeability:	0.00043059923336841166
Pgp-inhibitor:	0.001
Pgp-substrate:	0.338
Human Intestinal Absorption (HIA):	0.847
20% Bioavailability (F20%):	0.722
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	79.9679183959961%
Volume Distribution (VD):	0.491
Pgp-substrate:	12.421289443969727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.609
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	12.274
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.552
Drug-inuced Liver Injury (DILI):	0.831
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.068
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC113295

Natural Product ID:	NPC113295
*Common Name:**	Marlphenol E
IUPAC Name:	(2S)-2-[bis(3-hydroxy-4-methoxyphenyl)methyl]-4-hydroxy-3-(hydroxymethyl)butanoic acid
Synonyms:	Marlphenol E
Standard InCHIKey:	IFHDZGDDZBOJCI-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C20H24O8/c1-27-16-5-3-11(7-14(16)23)18(19(20(25)26)13(9-21)10-22)12-4-6-17(28-2)15(24)8-12/h3-8,13,18-19,21-24H,9-10H2,1-2H3,(H,25,26)/t19-/m1/s1
SMILES:	OCC([C@H](C(c1ccc(c(c1)O)OC)c1ccc(c(c1)O)OC)C(=O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334859
PubChem CID:	71577012
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462233]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23327759]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	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
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	73.5	ug.mL-1	PMID[544671]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	21.18	n.a.	PMID[544671]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3.47	ug.mL-1	PMID[544671]

☑ 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 NPC113295 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	289
0.1-0.2	1143
0.2-0.3	3033
0.3-0.4	7417
0.4-0.5	11532
0.5-0.6	3549
0.6-0.7	8907
0.7-0.8	5977
0.8-0.85	670
0.85-0.9	161
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC52664
0.9478	High Similarity	NPC100675
0.9466	High Similarity	NPC68779
0.9466	High Similarity	NPC4982
0.9466	High Similarity	NPC176814
0.9466	High Similarity	NPC300776
0.9466	High Similarity	NPC5310
0.9248	High Similarity	NPC470990
0.9179	High Similarity	NPC90431
0.9124	High Similarity	NPC31751
0.9124	High Similarity	NPC253481
0.9124	High Similarity	NPC253722
0.9084	High Similarity	NPC241354
0.907	High Similarity	NPC257589
0.907	High Similarity	NPC53305
0.907	High Similarity	NPC280767
0.9065	High Similarity	NPC223185
0.9062	High Similarity	NPC280704
0.9058	High Similarity	NPC470811
0.9058	High Similarity	NPC273657
0.9058	High Similarity	NPC477696
0.9058	High Similarity	NPC106920
0.9058	High Similarity	NPC477697
0.9051	High Similarity	NPC166137
0.9051	High Similarity	NPC29599
0.9051	High Similarity	NPC282291
0.9015	High Similarity	NPC319282
0.9015	High Similarity	NPC275724
0.9015	High Similarity	NPC137427
0.9015	High Similarity	NPC123196
0.9015	High Similarity	NPC65935
0.9015	High Similarity	NPC244246
0.9015	High Similarity	NPC311419
0.9015	High Similarity	NPC215941
0.9	High Similarity	NPC127937
0.9	High Similarity	NPC92207
0.8984	High Similarity	NPC85488
0.8971	High Similarity	NPC281780
0.8931	High Similarity	NPC223807
0.8929	High Similarity	NPC53884
0.8929	High Similarity	NPC258671
0.8913	High Similarity	NPC470991
0.8906	High Similarity	NPC177291
0.8906	High Similarity	NPC194416
0.8897	High Similarity	NPC120852
0.8897	High Similarity	NPC471988
0.8889	High Similarity	NPC67247
0.8864	High Similarity	NPC226661
0.8857	High Similarity	NPC304956
0.8855	High Similarity	NPC90128
0.8855	High Similarity	NPC303680
0.8855	High Similarity	NPC84076
0.8841	High Similarity	NPC147379
0.8828	High Similarity	NPC115466
0.8828	High Similarity	NPC245615
0.8828	High Similarity	NPC61604
0.8828	High Similarity	NPC473236
0.8828	High Similarity	NPC299706
0.8815	High Similarity	NPC475468
0.8811	High Similarity	NPC125570
0.8803	High Similarity	NPC221383
0.8803	High Similarity	NPC143892
0.8803	High Similarity	NPC283081
0.8803	High Similarity	NPC299090
0.8797	High Similarity	NPC304622
0.8788	High Similarity	NPC151167
0.8788	High Similarity	NPC20287
0.8788	High Similarity	NPC12022
0.8788	High Similarity	NPC165045
0.8788	High Similarity	NPC5018
0.8788	High Similarity	NPC293641
0.8788	High Similarity	NPC118533
0.8788	High Similarity	NPC123722
0.8788	High Similarity	NPC123228
0.8788	High Similarity	NPC20404
0.8788	High Similarity	NPC5428
0.8788	High Similarity	NPC276466
0.8777	High Similarity	NPC82336
0.8777	High Similarity	NPC78987
0.8769	High Similarity	NPC163083
0.876	High Similarity	NPC324571
0.876	High Similarity	NPC201777
0.876	High Similarity	NPC54872
0.876	High Similarity	NPC470212
0.876	High Similarity	NPC312675
0.876	High Similarity	NPC473853
0.876	High Similarity	NPC113865
0.876	High Similarity	NPC262156
0.876	High Similarity	NPC184651
0.876	High Similarity	NPC343720
0.8759	High Similarity	NPC476434
0.875	High Similarity	NPC95614
0.875	High Similarity	NPC165133
0.875	High Similarity	NPC56214
0.875	High Similarity	NPC242885
0.875	High Similarity	NPC227217
0.875	High Similarity	NPC117780
0.875	High Similarity	NPC471110
0.875	High Similarity	NPC135127
0.875	High Similarity	NPC232316
0.8741	High Similarity	NPC472969
0.8741	High Similarity	NPC1580
0.8731	High Similarity	NPC195292
0.8722	High Similarity	NPC278308
0.8712	High Similarity	NPC213552
0.8712	High Similarity	NPC120225
0.8712	High Similarity	NPC179777
0.8707	High Similarity	NPC38699
0.8705	High Similarity	NPC288452
0.8705	High Similarity	NPC289690
0.8699	High Similarity	NPC65591
0.8699	High Similarity	NPC178574
0.8686	High Similarity	NPC152209
0.8682	High Similarity	NPC207613
0.8681	High Similarity	NPC216223
0.8681	High Similarity	NPC477695
0.8681	High Similarity	NPC668
0.8681	High Similarity	NPC174512
0.8681	High Similarity	NPC55327
0.8681	High Similarity	NPC145569
0.8681	High Similarity	NPC293757
0.8681	High Similarity	NPC474965
0.8676	High Similarity	NPC327410
0.8672	High Similarity	NPC281298
0.8672	High Similarity	NPC310338
0.8657	High Similarity	NPC475875
0.8657	High Similarity	NPC83062
0.8649	High Similarity	NPC478055
0.8649	High Similarity	NPC163635
0.8639	High Similarity	NPC136757
0.8636	High Similarity	NPC3221
0.8636	High Similarity	NPC289459
0.8636	High Similarity	NPC148627
0.8633	High Similarity	NPC284409
0.863	High Similarity	NPC477699
0.863	High Similarity	NPC267091
0.8626	High Similarity	NPC31344
0.8626	High Similarity	NPC317769
0.8621	High Similarity	NPC158635
0.8621	High Similarity	NPC229882
0.8615	High Similarity	NPC38996
0.8615	High Similarity	NPC160380
0.8603	High Similarity	NPC239302
0.8601	High Similarity	NPC98356
0.8601	High Similarity	NPC3982
0.8594	High Similarity	NPC474040
0.8594	High Similarity	NPC205502
0.8594	High Similarity	NPC470626
0.8593	High Similarity	NPC174495
0.8593	High Similarity	NPC173308
0.8593	High Similarity	NPC92164
0.8593	High Similarity	NPC145305
0.8593	High Similarity	NPC241522
0.8593	High Similarity	NPC242807
0.8593	High Similarity	NPC64201
0.8593	High Similarity	NPC181079
0.8593	High Similarity	NPC142985
0.8593	High Similarity	NPC187998
0.8593	High Similarity	NPC153739
0.8593	High Similarity	NPC77040
0.8593	High Similarity	NPC42300
0.8593	High Similarity	NPC257582
0.8592	High Similarity	NPC46161
0.8592	High Similarity	NPC239608
0.8582	High Similarity	NPC131971
0.8582	High Similarity	NPC67467
0.8582	High Similarity	NPC307050
0.8582	High Similarity	NPC277458
0.8571	High Similarity	NPC110699
0.8571	High Similarity	NPC203351
0.8571	High Similarity	NPC106055
0.8571	High Similarity	NPC322021
0.8571	High Similarity	NPC474784
0.8562	High Similarity	NPC477700
0.8562	High Similarity	NPC243891
0.8561	High Similarity	NPC308976
0.8561	High Similarity	NPC246704
0.8552	High Similarity	NPC476394
0.8552	High Similarity	NPC98809
0.8551	High Similarity	NPC44245
0.8551	High Similarity	NPC477301
0.8551	High Similarity	NPC211386
0.8551	High Similarity	NPC72796
0.854	High Similarity	NPC129889
0.854	High Similarity	NPC205915
0.854	High Similarity	NPC307006
0.8529	High Similarity	NPC469480
0.8529	High Similarity	NPC474017
0.8529	High Similarity	NPC277804
0.8527	High Similarity	NPC299406
0.8527	High Similarity	NPC311595
0.8527	High Similarity	NPC24474
0.8516	High Similarity	NPC293619
0.8511	High Similarity	NPC19158
0.8511	High Similarity	NPC9218
0.8507	High Similarity	NPC281020
0.8503	High Similarity	NPC246566
0.8503	High Similarity	NPC95498
0.8503	High Similarity	NPC56184
0.8503	High Similarity	NPC75695

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 NPC113295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	786
0.2-0.3	1565
0.3-0.4	2463
0.4-0.5	2016
0.5-0.6	1115
0.6-0.7	771
0.7-0.8	175
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8382	Intermediate Similarity	NPD3027	Phase 3
0.8346	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD37	Approved
0.8289	Intermediate Similarity	NPD6234	Discontinued
0.8203	Intermediate Similarity	NPD5283	Phase 1
0.8194	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD4110	Phase 3
0.8158	Intermediate Similarity	NPD4965	Approved
0.8158	Intermediate Similarity	NPD4966	Approved
0.8158	Intermediate Similarity	NPD4967	Phase 2
0.8143	Intermediate Similarity	NPD6355	Discontinued
0.8071	Intermediate Similarity	NPD4060	Phase 1
0.8047	Intermediate Similarity	NPD228	Approved
0.8038	Intermediate Similarity	NPD7228	Approved
0.8015	Intermediate Similarity	NPD1283	Approved
0.8014	Intermediate Similarity	NPD6190	Approved
0.8	Intermediate Similarity	NPD6233	Phase 2
0.7971	Intermediate Similarity	NPD9494	Approved
0.7929	Intermediate Similarity	NPD6798	Discontinued
0.7922	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2438	Suspended
0.7917	Intermediate Similarity	NPD2935	Discontinued
0.7905	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD3022	Approved
0.7891	Intermediate Similarity	NPD3021	Approved
0.7857	Intermediate Similarity	NPD7095	Approved
0.7834	Intermediate Similarity	NPD7199	Phase 2
0.7832	Intermediate Similarity	NPD6653	Approved
0.7823	Intermediate Similarity	NPD4628	Phase 3
0.7823	Intermediate Similarity	NPD8166	Discontinued
0.782	Intermediate Similarity	NPD5536	Phase 2
0.7817	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2979	Phase 3
0.7817	Intermediate Similarity	NPD3620	Phase 2
0.7794	Intermediate Similarity	NPD1281	Approved
0.7785	Intermediate Similarity	NPD6232	Discontinued
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7746	Intermediate Similarity	NPD4062	Phase 3
0.774	Intermediate Similarity	NPD7266	Discontinued
0.7737	Intermediate Similarity	NPD1608	Approved
0.773	Intermediate Similarity	NPD7685	Pre-registration
0.7727	Intermediate Similarity	NPD1934	Approved
0.7721	Intermediate Similarity	NPD3847	Discontinued
0.7704	Intermediate Similarity	NPD5585	Approved
0.7698	Intermediate Similarity	NPD2797	Approved
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2801	Approved
0.7664	Intermediate Similarity	NPD1535	Discovery
0.7651	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5647	Approved
0.7639	Intermediate Similarity	NPD230	Phase 1
0.7639	Intermediate Similarity	NPD447	Suspended
0.763	Intermediate Similarity	NPD1894	Discontinued
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7625	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD8127	Discontinued
0.7609	Intermediate Similarity	NPD1481	Phase 2
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.758	Intermediate Similarity	NPD3882	Suspended
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1651	Approved
0.7568	Intermediate Similarity	NPD5958	Discontinued
0.7568	Intermediate Similarity	NPD4534	Discontinued
0.7564	Intermediate Similarity	NPD1465	Phase 2
0.7564	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3268	Approved
0.7537	Intermediate Similarity	NPD7157	Approved
0.7535	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7097	Phase 1
0.7518	Intermediate Similarity	NPD17	Approved
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.747	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD825	Approved
0.7448	Intermediate Similarity	NPD826	Approved
0.7445	Intermediate Similarity	NPD1357	Approved
0.7444	Intermediate Similarity	NPD7843	Approved
0.7439	Intermediate Similarity	NPD5844	Phase 1
0.7439	Intermediate Similarity	NPD7054	Approved
0.7432	Intermediate Similarity	NPD2531	Phase 2
0.7432	Intermediate Similarity	NPD6032	Approved
0.7429	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4359	Approved
0.7419	Intermediate Similarity	NPD3455	Phase 2
0.7405	Intermediate Similarity	NPD2684	Approved
0.7394	Intermediate Similarity	NPD7472	Approved
0.7391	Intermediate Similarity	NPD4626	Approved
0.7386	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7028	Phase 2
0.7355	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1653	Approved
0.7342	Intermediate Similarity	NPD8455	Phase 2
0.7338	Intermediate Similarity	NPD6273	Approved
0.7329	Intermediate Similarity	NPD4140	Approved
0.7325	Intermediate Similarity	NPD6386	Approved
0.7325	Intermediate Similarity	NPD6385	Approved
0.7325	Intermediate Similarity	NPD6873	Phase 2
0.732	Intermediate Similarity	NPD1511	Approved
0.7315	Intermediate Similarity	NPD4476	Approved
0.7315	Intermediate Similarity	NPD4477	Approved
0.7313	Intermediate Similarity	NPD5535	Approved
0.731	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD2983	Phase 2
0.7305	Intermediate Similarity	NPD2982	Phase 2
0.7292	Intermediate Similarity	NPD2614	Approved
0.7286	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD258	Approved
0.7273	Intermediate Similarity	NPD257	Approved
0.7267	Intermediate Similarity	NPD6002	Phase 3
0.7267	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD6004	Phase 3
0.7267	Intermediate Similarity	NPD6005	Phase 3
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.726	Intermediate Similarity	NPD8032	Phase 2
0.726	Intermediate Similarity	NPD6663	Approved
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD6797	Phase 2
0.7237	Intermediate Similarity	NPD7003	Approved
0.7234	Intermediate Similarity	NPD2981	Phase 2
0.7226	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD3018	Phase 2
0.7222	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3496	Discontinued
0.7206	Intermediate Similarity	NPD2629	Approved
0.7205	Intermediate Similarity	NPD7075	Discontinued
0.7203	Intermediate Similarity	NPD3267	Approved
0.7203	Intermediate Similarity	NPD3266	Approved
0.7203	Intermediate Similarity	NPD6362	Approved
0.7202	Intermediate Similarity	NPD7251	Discontinued
0.7197	Intermediate Similarity	NPD1358	Approved
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5242	Approved
0.7194	Intermediate Similarity	NPD5691	Approved
0.7192	Intermediate Similarity	NPD5111	Phase 2
0.7192	Intermediate Similarity	NPD5110	Phase 2
0.7192	Intermediate Similarity	NPD3764	Approved
0.7192	Intermediate Similarity	NPD5109	Approved
0.7188	Intermediate Similarity	NPD5402	Approved
0.7188	Intermediate Similarity	NPD3020	Approved
0.7175	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4908	Phase 1
0.7172	Intermediate Similarity	NPD6832	Phase 2
0.7171	Intermediate Similarity	NPD3060	Approved
0.7171	Intermediate Similarity	NPD6674	Discontinued
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7171	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1933	Approved
0.7162	Intermediate Similarity	NPD4618	Approved
0.7162	Intermediate Similarity	NPD4622	Approved
0.7162	Intermediate Similarity	NPD555	Phase 2
0.7161	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7808	Phase 3
0.7153	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD259	Phase 1
0.7143	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD4870	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD3019	Approved
0.7134	Intermediate Similarity	NPD3686	Approved
0.7134	Intermediate Similarity	NPD3687	Approved
0.7133	Intermediate Similarity	NPD1876	Approved
0.7125	Intermediate Similarity	NPD7819	Suspended
0.7125	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3750	Approved
0.7124	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3134	Approved
0.7117	Intermediate Similarity	NPD5494	Approved
0.7113	Intermediate Similarity	NPD9269	Phase 2
0.7113	Intermediate Similarity	NPD3972	Approved
0.7111	Intermediate Similarity	NPD7680	Approved
0.7107	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2424	Discontinued
0.7099	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4357	Discontinued
0.7097	Intermediate Similarity	NPD6799	Approved
0.7095	Intermediate Similarity	NPD943	Approved
0.7095	Intermediate Similarity	NPD1558	Phase 1
0.7086	Intermediate Similarity	NPD2239	Approved
0.7086	Intermediate Similarity	NPD2240	Approved
0.7086	Intermediate Similarity	NPD9570	Approved
0.7086	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD987	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