NPASS Compound

Structure

CID311595 OpenBabel06191716122D 21 21 0 0 1 0 0 0 0 0999 V2000 6.9282 6.0000 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 6.0622 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 1.7321 -1.0000 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 0.8660 -1.5000 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 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 4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -1.5000 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 3 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 14 18 1 6 0 0 0 15 19 1 6 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.2
Volume:	321.283
LogP:	3.248
LogD:	3.099
LogS:	-3.78
# Rotatable Bonds:	10
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	2.848
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.592
MDCK Permeability:	2.4940432922448963e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.732
Plasma Protein Binding (PPB):	91.90788269042969%
Volume Distribution (VD):	2.64
Pgp-substrate:	7.374539375305176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.701
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.69
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.556
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.242
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	13.055
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.943
Carcinogencity:	0.133
Eye Corrosion:	0.706
Eye Irritation:	0.967
Respiratory Toxicity:	0.763

Download Data

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

Natural Product: NPC311595

Natural Product ID:	NPC311595
*Common Name:**	(3R,5S)-1-(4-Hydroxy-3-Methoxyphenyl)Decane-3,5-Diol
IUPAC Name:	(3R,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol
Synonyms:
Standard InCHIKey:	QYXKQNMJTHPKBP-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C17H28O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14-15,18-20H,3-7,9,12H2,1-2H3/t14-,15+/m0/s1
SMILES:	CCCCC[C@@H](C[C@@H](CCc1ccc(c(c1)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071442
PubChem CID:	11369949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols [CHEMONTID:0001706] Gingerdiols

*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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22789014]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	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
MIC	2
Others	8

Activity Type	# Activity
Organism	3
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>=	128.0	ug.mL-1	PMID[463379]
NPT2	Others	Unspecified		FC	=	2.0	n.a.	PMID[463379]
NPT2	Others	Unspecified		FC	=	1.0	n.a.	PMID[463379]
NPT2	Others	Unspecified		FICI	=	1.0	n.a.	PMID[463379]
NPT2	Others	Unspecified		FICI	=	2.0	n.a.	PMID[463379]
NPT22712	ORGANISM	Hymenolepis nana	Hymenolepis nana	EC	=	0.001	mM	PMID[463380]

☑ 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 NPC311595 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	296
0.1-0.2	1373
0.2-0.3	4753
0.3-0.4	12678
0.4-0.5	5543
0.5-0.6	5684
0.6-0.7	8227
0.7-0.8	3144
0.8-0.85	624
0.85-0.9	288
0.9-0.95	73
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24474
0.982	High Similarity	NPC164386
0.9737	High Similarity	NPC54872
0.9737	High Similarity	NPC343720
0.9737	High Similarity	NPC312675
0.9737	High Similarity	NPC473853
0.9737	High Similarity	NPC262156
0.9737	High Similarity	NPC184651
0.9737	High Similarity	NPC470212
0.9737	High Similarity	NPC324571
0.9737	High Similarity	NPC113865
0.9649	High Similarity	NPC207613
0.9565	High Similarity	NPC476343
0.9402	High Similarity	NPC471693
0.9402	High Similarity	NPC280704
0.9397	High Similarity	NPC470804
0.9391	High Similarity	NPC148615
0.9391	High Similarity	NPC35071
0.9391	High Similarity	NPC177475
0.9386	High Similarity	NPC474214
0.9386	High Similarity	NPC255675
0.9386	High Similarity	NPC470626
0.9316	High Similarity	NPC85488
0.9304	High Similarity	NPC320987
0.9304	High Similarity	NPC135961
0.9304	High Similarity	NPC181969
0.9304	High Similarity	NPC474320
0.9298	High Similarity	NPC293619
0.9279	High Similarity	NPC139617
0.9279	High Similarity	NPC156840
0.9279	High Similarity	NPC173746
0.9279	High Similarity	NPC8547
0.9279	High Similarity	NPC78918
0.9279	High Similarity	NPC257124
0.925	High Similarity	NPC118533
0.925	High Similarity	NPC165045
0.9244	High Similarity	NPC148627
0.9231	High Similarity	NPC127389
0.9231	High Similarity	NPC290451
0.9224	High Similarity	NPC117780
0.9224	High Similarity	NPC227217
0.9224	High Similarity	NPC165133
0.9224	High Similarity	NPC242885
0.9224	High Similarity	NPC232316
0.9224	High Similarity	NPC95614
0.9224	High Similarity	NPC56214
0.9211	High Similarity	NPC221049
0.9189	High Similarity	NPC137685
0.9174	High Similarity	NPC206615
0.9174	High Similarity	NPC186843
0.9174	High Similarity	NPC98631
0.9174	High Similarity	NPC470213
0.9174	High Similarity	NPC252307
0.9174	High Similarity	NPC245826
0.9174	High Similarity	NPC474178
0.916	High Similarity	NPC293701
0.916	High Similarity	NPC48990
0.916	High Similarity	NPC114901
0.9153	High Similarity	NPC209567
0.9138	High Similarity	NPC310338
0.9138	High Similarity	NPC281298
0.9099	High Similarity	NPC233731
0.9099	High Similarity	NPC36108
0.9099	High Similarity	NPC7097
0.9099	High Similarity	NPC246358
0.9098	High Similarity	NPC475875
0.9098	High Similarity	NPC170844
0.9098	High Similarity	NPC476968
0.9098	High Similarity	NPC212015
0.9091	High Similarity	NPC163332
0.9091	High Similarity	NPC12022
0.9091	High Similarity	NPC292056
0.9091	High Similarity	NPC118787
0.9091	High Similarity	NPC293641
0.9091	High Similarity	NPC111247
0.9091	High Similarity	NPC20287
0.9091	High Similarity	NPC20404
0.9091	High Similarity	NPC319625
0.9091	High Similarity	NPC183181
0.9091	High Similarity	NPC147821
0.9091	High Similarity	NPC5428
0.9091	High Similarity	NPC41706
0.9083	High Similarity	NPC194519
0.9076	High Similarity	NPC31344
0.9076	High Similarity	NPC220598
0.9076	High Similarity	NPC165375
0.9076	High Similarity	NPC317769
0.9068	High Similarity	NPC38996
0.9068	High Similarity	NPC49341
0.9068	High Similarity	NPC160380
0.9052	High Similarity	NPC474040
0.9024	High Similarity	NPC77040
0.9024	High Similarity	NPC92164
0.9024	High Similarity	NPC242807
0.9024	High Similarity	NPC153739
0.9024	High Similarity	NPC145305
0.9024	High Similarity	NPC42300
0.9024	High Similarity	NPC241522
0.9024	High Similarity	NPC257582
0.9024	High Similarity	NPC187998
0.9024	High Similarity	NPC174495
0.9024	High Similarity	NPC64201
0.9016	High Similarity	NPC278308
0.9008	High Similarity	NPC191037
0.9008	High Similarity	NPC178284
0.9008	High Similarity	NPC58607
0.8952	High Similarity	NPC474017
0.8952	High Similarity	NPC277804
0.8943	High Similarity	NPC5851
0.8943	High Similarity	NPC86030
0.8938	High Similarity	NPC195873
0.8926	High Similarity	NPC298757
0.8926	High Similarity	NPC233410
0.8926	High Similarity	NPC117214
0.8926	High Similarity	NPC57490
0.8926	High Similarity	NPC193544
0.8926	High Similarity	NPC251855
0.8926	High Similarity	NPC203133
0.8926	High Similarity	NPC472093
0.8926	High Similarity	NPC221077
0.8926	High Similarity	NPC17943
0.8926	High Similarity	NPC208950
0.8926	High Similarity	NPC475169
0.8926	High Similarity	NPC116907
0.8919	High Similarity	NPC227894
0.8917	High Similarity	NPC228922
0.8917	High Similarity	NPC163083
0.8917	High Similarity	NPC197757
0.8908	High Similarity	NPC201777
0.8898	High Similarity	NPC229401
0.888	High Similarity	NPC253105
0.888	High Similarity	NPC201587
0.8871	High Similarity	NPC137427
0.8871	High Similarity	NPC311419
0.8871	High Similarity	NPC244246
0.8871	High Similarity	NPC215941
0.8871	High Similarity	NPC65935
0.8871	High Similarity	NPC472338
0.8871	High Similarity	NPC123196
0.8871	High Similarity	NPC143483
0.8871	High Similarity	NPC319282
0.8871	High Similarity	NPC275724
0.8862	High Similarity	NPC277458
0.8862	High Similarity	NPC129570
0.8862	High Similarity	NPC128208
0.8862	High Similarity	NPC21867
0.8862	High Similarity	NPC184733
0.8862	High Similarity	NPC470084
0.8862	High Similarity	NPC307050
0.8862	High Similarity	NPC72529
0.8862	High Similarity	NPC45774
0.8862	High Similarity	NPC282703
0.8862	High Similarity	NPC11258
0.886	High Similarity	NPC165646
0.8843	High Similarity	NPC94276
0.8843	High Similarity	NPC146886
0.8843	High Similarity	NPC20443
0.8843	High Similarity	NPC60517
0.8843	High Similarity	NPC109822
0.8833	High Similarity	NPC71090
0.8833	High Similarity	NPC41562
0.8814	High Similarity	NPC20674
0.881	High Similarity	NPC475840
0.8803	High Similarity	NPC86947
0.88	High Similarity	NPC472597
0.88	High Similarity	NPC40432
0.88	High Similarity	NPC65942
0.88	High Similarity	NPC115207
0.88	High Similarity	NPC158079
0.88	High Similarity	NPC470096
0.88	High Similarity	NPC228346
0.88	High Similarity	NPC161557
0.88	High Similarity	NPC7171
0.88	High Similarity	NPC27843
0.88	High Similarity	NPC470095
0.88	High Similarity	NPC248307
0.879	High Similarity	NPC158477
0.878	High Similarity	NPC74817
0.878	High Similarity	NPC82679
0.878	High Similarity	NPC124452
0.878	High Similarity	NPC324112
0.878	High Similarity	NPC293054
0.878	High Similarity	NPC169474
0.878	High Similarity	NPC106511
0.878	High Similarity	NPC127587
0.878	High Similarity	NPC236791
0.878	High Similarity	NPC246620
0.878	High Similarity	NPC282000
0.878	High Similarity	NPC159968
0.8772	High Similarity	NPC257430
0.8772	High Similarity	NPC179002
0.8772	High Similarity	NPC187583
0.8772	High Similarity	NPC55300
0.877	High Similarity	NPC228771
0.877	High Similarity	NPC53305
0.877	High Similarity	NPC29008
0.877	High Similarity	NPC266705
0.877	High Similarity	NPC257589
0.877	High Similarity	NPC9067
0.877	High Similarity	NPC280767

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 NPC311595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	893
0.2-0.3	1841
0.3-0.4	2675
0.4-0.5	1679
0.5-0.6	993
0.6-0.7	639
0.7-0.8	150
0.8-0.85	13
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9279	High Similarity	NPD228	Approved
0.9098	High Similarity	NPD3027	Phase 3
0.8621	High Similarity	NPD5283	Phase 1
0.8509	High Similarity	NPD2684	Approved
0.85	High Similarity	NPD1357	Approved
0.8455	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD3620	Phase 2
0.8376	Intermediate Similarity	NPD7843	Approved
0.8319	Intermediate Similarity	NPD7157	Approved
0.8295	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD1613	Approved
0.8276	Intermediate Similarity	NPD3021	Approved
0.8276	Intermediate Similarity	NPD3022	Approved
0.8103	Intermediate Similarity	NPD290	Approved
0.8077	Intermediate Similarity	NPD2674	Phase 3
0.7984	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD291	Approved
0.7928	Intermediate Similarity	NPD9296	Approved
0.7907	Intermediate Similarity	NPD9494	Approved
0.7907	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD5536	Phase 2
0.7863	Intermediate Similarity	NPD3144	Approved
0.7863	Intermediate Similarity	NPD3145	Approved
0.7857	Intermediate Similarity	NPD3705	Approved
0.781	Intermediate Similarity	NPD3060	Approved
0.7744	Intermediate Similarity	NPD4060	Phase 1
0.7734	Intermediate Similarity	NPD2982	Phase 2
0.7734	Intermediate Similarity	NPD2983	Phase 2
0.7734	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6671	Approved
0.7669	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD2981	Phase 2
0.7634	Intermediate Similarity	NPD3018	Phase 2
0.7612	Intermediate Similarity	NPD1558	Phase 1
0.7591	Intermediate Similarity	NPD2161	Phase 2
0.7559	Intermediate Similarity	NPD6516	Phase 2
0.7559	Intermediate Similarity	NPD5846	Approved
0.7559	Intermediate Similarity	NPD4626	Approved
0.7557	Intermediate Similarity	NPD6584	Phase 3
0.7554	Intermediate Similarity	NPD4162	Approved
0.7554	Intermediate Similarity	NPD4237	Approved
0.7554	Intermediate Similarity	NPD5177	Phase 3
0.7554	Intermediate Similarity	NPD4236	Phase 3
0.7544	Intermediate Similarity	NPD2859	Approved
0.7544	Intermediate Similarity	NPD2860	Approved
0.7536	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD3020	Approved
0.75	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7483	Intermediate Similarity	NPD7526	Approved
0.7483	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD52	Approved
0.748	Intermediate Similarity	NPD821	Approved
0.7463	Intermediate Similarity	NPD5109	Approved
0.7463	Intermediate Similarity	NPD5110	Phase 2
0.7463	Intermediate Similarity	NPD5111	Phase 2
0.7462	Intermediate Similarity	NPD3685	Discontinued
0.7456	Intermediate Similarity	NPD2934	Approved
0.7456	Intermediate Similarity	NPD2933	Approved
0.7456	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5241	Discontinued
0.7445	Intermediate Similarity	NPD4538	Approved
0.7445	Intermediate Similarity	NPD4536	Approved
0.7445	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4908	Phase 1
0.7444	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1091	Approved
0.7429	Intermediate Similarity	NPD6674	Discontinued
0.7426	Intermediate Similarity	NPD3657	Discovery
0.7426	Intermediate Similarity	NPD5735	Approved
0.7422	Intermediate Similarity	NPD9384	Approved
0.7422	Intermediate Similarity	NPD9381	Approved
0.7417	Intermediate Similarity	NPD968	Approved
0.7415	Intermediate Similarity	NPD1934	Approved
0.7405	Intermediate Similarity	NPD8651	Approved
0.7391	Intermediate Similarity	NPD844	Approved
0.7388	Intermediate Similarity	NPD7095	Approved
0.7385	Intermediate Similarity	NPD2231	Phase 2
0.7385	Intermediate Similarity	NPD2235	Phase 2
0.7379	Intermediate Similarity	NPD1653	Approved
0.7377	Intermediate Similarity	NPD5451	Approved
0.7377	Intermediate Similarity	NPD556	Approved
0.7376	Intermediate Similarity	NPD6331	Phase 2
0.7365	Intermediate Similarity	NPD2978	Approved
0.7365	Intermediate Similarity	NPD2977	Approved
0.7364	Intermediate Similarity	NPD3496	Discontinued
0.7353	Intermediate Similarity	NPD2238	Phase 2
0.7348	Intermediate Similarity	NPD3094	Phase 2
0.7344	Intermediate Similarity	NPD5691	Approved
0.7339	Intermediate Similarity	NPD9377	Approved
0.7339	Intermediate Similarity	NPD9379	Approved
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.7328	Intermediate Similarity	NPD6583	Phase 3
0.7328	Intermediate Similarity	NPD6582	Phase 2
0.7328	Intermediate Similarity	NPD9622	Approved
0.7308	Intermediate Similarity	NPD3092	Approved
0.7308	Intermediate Similarity	NPD1610	Phase 2
0.7305	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6355	Discontinued
0.7293	Intermediate Similarity	NPD3691	Phase 2
0.7293	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3690	Phase 2
0.7287	Intermediate Similarity	NPD2667	Approved
0.7287	Intermediate Similarity	NPD2668	Approved
0.7286	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD2922	Phase 1
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.7266	Intermediate Similarity	NPD5960	Phase 3
0.7266	Intermediate Similarity	NPD5588	Approved
0.7266	Intermediate Similarity	NPD3091	Approved
0.726	Intermediate Similarity	NPD3687	Approved
0.726	Intermediate Similarity	NPD3686	Approved
0.7252	Intermediate Similarity	NPD2233	Approved
0.7252	Intermediate Similarity	NPD2230	Approved
0.7252	Intermediate Similarity	NPD2232	Approved
0.7248	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2424	Discontinued
0.7234	Intermediate Similarity	NPD7153	Discontinued
0.7231	Intermediate Similarity	NPD3847	Discontinued
0.7227	Intermediate Similarity	NPD846	Approved
0.7227	Intermediate Similarity	NPD940	Approved
0.7226	Intermediate Similarity	NPD4140	Approved
0.7226	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1818	Approved
0.7218	Intermediate Similarity	NPD1820	Approved
0.7218	Intermediate Similarity	NPD1819	Approved
0.7218	Intermediate Similarity	NPD1817	Approved
0.7206	Intermediate Similarity	NPD5718	Phase 2
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5535	Approved
0.7197	Intermediate Similarity	NPD5327	Phase 3
0.7197	Intermediate Similarity	NPD4749	Approved
0.7194	Intermediate Similarity	NPD6896	Approved
0.7194	Intermediate Similarity	NPD6895	Approved
0.7193	Intermediate Similarity	NPD9365	Approved
0.7185	Intermediate Similarity	NPD600	Approved
0.7185	Intermediate Similarity	NPD596	Approved
0.7181	Intermediate Similarity	NPD37	Approved
0.7179	Intermediate Similarity	NPD288	Approved
0.7177	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6234	Discontinued
0.7164	Intermediate Similarity	NPD4624	Approved
0.7164	Intermediate Similarity	NPD9619	Approved
0.7164	Intermediate Similarity	NPD558	Phase 2
0.7164	Intermediate Similarity	NPD9620	Approved
0.7164	Intermediate Similarity	NPD9621	Approved
0.7163	Intermediate Similarity	NPD5763	Approved
0.7163	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5762	Approved
0.7161	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6166	Phase 2
0.7153	Intermediate Similarity	NPD4062	Phase 3
0.7153	Intermediate Similarity	NPD839	Approved
0.7153	Intermediate Similarity	NPD840	Approved
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4535	Phase 3
0.7133	Intermediate Similarity	NPD2801	Approved
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7132	Intermediate Similarity	NPD3164	Approved
0.7132	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3165	Approved
0.7132	Intermediate Similarity	NPD3166	Approved
0.7132	Intermediate Similarity	NPD3179	Approved
0.7132	Intermediate Similarity	NPD3167	Approved
0.7132	Intermediate Similarity	NPD3180	Approved
0.7117	Intermediate Similarity	NPD111	Approved
0.7101	Intermediate Similarity	NPD3059	Approved
0.7101	Intermediate Similarity	NPD3061	Approved
0.7101	Intermediate Similarity	NPD825	Approved
0.7101	Intermediate Similarity	NPD3062	Approved
0.7101	Intermediate Similarity	NPD826	Approved
0.7095	Intermediate Similarity	NPD4005	Discontinued
0.7092	Intermediate Similarity	NPD2935	Discontinued
0.7086	Intermediate Similarity	NPD2563	Approved
0.7086	Intermediate Similarity	NPD2560	Approved
0.7083	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2677	Approved
0.7083	Intermediate Similarity	NPD6190	Approved
0.7083	Intermediate Similarity	NPD2219	Phase 1
0.708	Intermediate Similarity	NPD601	Approved
0.708	Intermediate Similarity	NPD598	Approved
0.708	Intermediate Similarity	NPD597	Approved
0.7077	Intermediate Similarity	NPD1651	Approved
0.7071	Intermediate Similarity	NPD6111	Discontinued
0.7068	Intermediate Similarity	NPD1669	Approved
0.7068	Intermediate Similarity	NPD3676	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