NPASS Compound

Structure

CID7483 OpenBabel06191715332D 36 38 0 0 0 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 4.3301 -2.5000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 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 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 1.7321 2.0000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 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 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 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 -0.8660 0.5000 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 0.0000 0.0000 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 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 35 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 23 2 0 0 0 0 15 18 1 0 0 0 0 15 30 1 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 31 1 0 0 0 0 22 29 2 0 0 0 0 22 32 1 0 0 0 0 23 25 1 0 0 0 0 23 36 1 0 0 0 0 24 26 2 0 0 0 0 24 36 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 33 1 0 0 0 0 28 34 2 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.23
Volume:	519.638
LogP:	5.643
LogD:	3.336
LogS:	-2.761
# Rotatable Bonds:	9
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	3.436
Fsp3:	0.345
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.898
MDCK Permeability:	9.127742487180512e-06
Pgp-inhibitor:	0.586
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.601
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.764

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.63789367675781%
Volume Distribution (VD):	0.417
Pgp-substrate:	1.6362603902816772%

ADMET: Metabolism

CYP1A2-inhibitor:	0.573
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.669
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.794
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	3.645
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.242
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.929
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.829
Respiratory Toxicity:	0.277

Download Data

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

Natural Product: NPC7483

Natural Product ID:	NPC7483
*Common Name:**	Cowanol
IUPAC Name:	1-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,6,8-trihydroxy-7-[(Z)-4-hydroxy-3-methylbut-2-enyl]-2-methoxyxanthen-9-one
Synonyms:	Cowanol
Standard InCHIKey:	BXFCPUCGPCDZKT-XXGRXQMWSA-N
Standard InCHI:	InChI=1S/C29H34O7/c1-16(2)7-6-8-17(3)9-12-20-25-23(14-22(32)29(20)35-5)36-24-13-21(31)19(11-10-18(4)15-30)27(33)26(24)28(25)34/h7,9-10,13-14,30-33H,6,8,11-12,15H2,1-5H3/b17-9+,18-10-
SMILES:	CC(=CCC/C(=C/Cc1c2c(cc(c1OC)O)oc1cc(c(C/C=C(/C)CO)c(c1c2=O)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463408
PubChem CID:	10480887
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

*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
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608849]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	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
IC50	2
Others	8

Activity Type	# Activity
Cell Line	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[520126]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[520126]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	11980.0	nM	PMID[520127]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[520126]
NPT2	Others	Unspecified		Inhibition	=	30.5	%	PMID[520126]
NPT2	Others	Unspecified		Inhibition	=	69.6	%	PMID[520126]
NPT2	Others	Unspecified		Inhibition	=	93.1	%	PMID[520126]
NPT2	Others	Unspecified		IC50	=	310.0	molar ratio	PMID[520126]

☑ 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 NPC7483 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	443
0.1-0.2	1691
0.2-0.3	3933
0.3-0.4	9973
0.4-0.5	8556
0.5-0.6	3545
0.6-0.7	5006
0.7-0.8	5189
0.8-0.85	2495
0.85-0.9	1298
0.9-0.95	508
0.95-1	60

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC40491
0.987	High Similarity	NPC278052
0.9805	High Similarity	NPC14353
0.9805	High Similarity	NPC475886
0.9805	High Similarity	NPC228785
0.9805	High Similarity	NPC320359
0.9805	High Similarity	NPC56085
0.9805	High Similarity	NPC474287
0.9744	High Similarity	NPC236132
0.9742	High Similarity	NPC474187
0.9742	High Similarity	NPC474351
0.9742	High Similarity	NPC61010
0.9742	High Similarity	NPC474186
0.9742	High Similarity	NPC475883
0.974	High Similarity	NPC100123
0.9684	High Similarity	NPC477154
0.9684	High Similarity	NPC117854
0.9684	High Similarity	NPC6588
0.9682	High Similarity	NPC326520
0.9675	High Similarity	NPC217677
0.9675	High Similarity	NPC300727
0.9675	High Similarity	NPC241904
0.9675	High Similarity	NPC236796
0.9675	High Similarity	NPC165977
0.962	High Similarity	NPC170245
0.962	High Similarity	NPC39091
0.9618	High Similarity	NPC220313
0.9618	High Similarity	NPC248638
0.9618	High Similarity	NPC152659
0.9618	High Similarity	NPC236521
0.9613	High Similarity	NPC329091
0.9613	High Similarity	NPC476242
0.961	High Similarity	NPC142339
0.961	High Similarity	NPC274730
0.9557	High Similarity	NPC275780
0.9557	High Similarity	NPC472450
0.9557	High Similarity	NPC475888
0.9557	High Similarity	NPC239752
0.9554	High Similarity	NPC25152
0.9554	High Similarity	NPC201800
0.9554	High Similarity	NPC211107
0.9551	High Similarity	NPC36217
0.9551	High Similarity	NPC119224
0.9551	High Similarity	NPC321399
0.9548	High Similarity	NPC262286
0.9548	High Similarity	NPC36852
0.9548	High Similarity	NPC78225
0.9548	High Similarity	NPC223787
0.9548	High Similarity	NPC469584
0.9494	High Similarity	NPC23298
0.9494	High Similarity	NPC189473
0.9494	High Similarity	NPC197168
0.9494	High Similarity	NPC475985
0.9494	High Similarity	NPC41301
0.9494	High Similarity	NPC270837
0.9494	High Similarity	NPC474240
0.949	High Similarity	NPC266314
0.949	High Similarity	NPC32694
0.9487	High Similarity	NPC250214
0.9487	High Similarity	NPC95936
0.9487	High Similarity	NPC210459
0.9484	High Similarity	NPC470328
0.9484	High Similarity	NPC191146
0.9484	High Similarity	NPC68093
0.9484	High Similarity	NPC209614
0.9484	High Similarity	NPC138243
0.9484	High Similarity	NPC472626
0.9481	High Similarity	NPC89474
0.9434	High Similarity	NPC293319
0.9434	High Similarity	NPC473286
0.9434	High Similarity	NPC25361
0.943	High Similarity	NPC294965
0.943	High Similarity	NPC472964
0.943	High Similarity	NPC229632
0.9427	High Similarity	NPC299436
0.9427	High Similarity	NPC235018
0.9427	High Similarity	NPC472630
0.9427	High Similarity	NPC200746
0.9427	High Similarity	NPC45146
0.9427	High Similarity	NPC472631
0.9423	High Similarity	NPC156057
0.9423	High Similarity	NPC96167
0.9423	High Similarity	NPC472598
0.9423	High Similarity	NPC162869
0.9423	High Similarity	NPC245758
0.9423	High Similarity	NPC472911
0.9423	High Similarity	NPC474208
0.9423	High Similarity	NPC474836
0.9423	High Similarity	NPC475267
0.9423	High Similarity	NPC474055
0.9423	High Similarity	NPC472910
0.9423	High Similarity	NPC136674
0.9423	High Similarity	NPC222814
0.9423	High Similarity	NPC472913
0.9423	High Similarity	NPC48208
0.9423	High Similarity	NPC472914
0.9419	High Similarity	NPC470327
0.9419	High Similarity	NPC113906
0.9419	High Similarity	NPC45849
0.9419	High Similarity	NPC200761
0.9419	High Similarity	NPC477503
0.9383	High Similarity	NPC260263
0.9375	High Similarity	NPC37870
0.9375	High Similarity	NPC470462
0.9375	High Similarity	NPC472449
0.9371	High Similarity	NPC186686
0.9371	High Similarity	NPC146134
0.9371	High Similarity	NPC474350
0.9371	High Similarity	NPC470459
0.9367	High Similarity	NPC474239
0.9367	High Similarity	NPC66288
0.9367	High Similarity	NPC472634
0.9363	High Similarity	NPC85121
0.9363	High Similarity	NPC235448
0.9359	High Similarity	NPC472916
0.9359	High Similarity	NPC278778
0.9359	High Similarity	NPC291878
0.9359	High Similarity	NPC255106
0.9359	High Similarity	NPC195796
0.9359	High Similarity	NPC235165
0.9359	High Similarity	NPC35038
0.9355	High Similarity	NPC298692
0.9351	High Similarity	NPC202157
0.9317	High Similarity	NPC474024
0.9317	High Similarity	NPC470456
0.9317	High Similarity	NPC158761
0.9317	High Similarity	NPC218226
0.9313	High Similarity	NPC470457
0.9308	High Similarity	NPC470694
0.9308	High Similarity	NPC474150
0.9308	High Similarity	NPC329760
0.9308	High Similarity	NPC52204
0.9308	High Similarity	NPC474162
0.9308	High Similarity	NPC472448
0.9308	High Similarity	NPC83922
0.9308	High Similarity	NPC220912
0.9308	High Similarity	NPC81679
0.9304	High Similarity	NPC282009
0.9304	High Similarity	NPC139036
0.9304	High Similarity	NPC287328
0.9304	High Similarity	NPC174953
0.9304	High Similarity	NPC472902
0.9304	High Similarity	NPC246478
0.9304	High Similarity	NPC204290
0.9304	High Similarity	NPC263449
0.9304	High Similarity	NPC471973
0.9304	High Similarity	NPC476980
0.9304	High Similarity	NPC80375
0.9304	High Similarity	NPC470326
0.9299	High Similarity	NPC99597
0.9299	High Similarity	NPC470402
0.9299	High Similarity	NPC78103
0.9299	High Similarity	NPC299520
0.9299	High Similarity	NPC129684
0.9299	High Similarity	NPC27337
0.9299	High Similarity	NPC181960
0.9299	High Similarity	NPC291508
0.9299	High Similarity	NPC472963
0.9299	High Similarity	NPC210084
0.9295	High Similarity	NPC57674
0.9295	High Similarity	NPC2928
0.9295	High Similarity	NPC230149
0.9295	High Similarity	NPC168247
0.9295	High Similarity	NPC226025
0.9295	High Similarity	NPC117992
0.9295	High Similarity	NPC472909
0.9295	High Similarity	NPC321779
0.9295	High Similarity	NPC130589
0.9295	High Similarity	NPC67396
0.9295	High Similarity	NPC213622
0.9295	High Similarity	NPC134287
0.9295	High Similarity	NPC152951
0.9295	High Similarity	NPC37392
0.929	High Similarity	NPC120537
0.929	High Similarity	NPC471982
0.929	High Similarity	NPC106976
0.929	High Similarity	NPC249570
0.929	High Similarity	NPC101996
0.929	High Similarity	NPC180234
0.929	High Similarity	NPC199100
0.9286	High Similarity	NPC151473
0.9255	High Similarity	NPC472452
0.9255	High Similarity	NPC43319
0.925	High Similarity	NPC329669
0.925	High Similarity	NPC273959
0.925	High Similarity	NPC18100
0.925	High Similarity	NPC473313
0.925	High Similarity	NPC472278
0.925	High Similarity	NPC207690
0.925	High Similarity	NPC124038
0.9245	High Similarity	NPC471499
0.9245	High Similarity	NPC471211
0.9245	High Similarity	NPC308992
0.9245	High Similarity	NPC29876
0.9245	High Similarity	NPC134783
0.9245	High Similarity	NPC474038
0.9245	High Similarity	NPC167678
0.9245	High Similarity	NPC26326
0.9245	High Similarity	NPC228383
0.9245	High Similarity	NPC472632

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 NPC7483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	964
0.2-0.3	1860
0.3-0.4	2654
0.4-0.5	1800
0.5-0.6	896
0.6-0.7	415
0.7-0.8	125
0.8-0.85	30
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD2393	Clinical (unspecified phase)
0.9231	High Similarity	NPD2801	Approved
0.9167	High Similarity	NPD1934	Approved
0.8841	High Similarity	NPD6168	Clinical (unspecified phase)
0.8841	High Similarity	NPD6167	Clinical (unspecified phase)
0.8841	High Similarity	NPD6166	Phase 2
0.8827	High Similarity	NPD5494	Approved
0.8758	High Similarity	NPD3882	Suspended
0.8743	High Similarity	NPD7074	Phase 3
0.8683	High Similarity	NPD5844	Phase 1
0.8683	High Similarity	NPD7054	Approved
0.8675	High Similarity	NPD7473	Discontinued
0.8654	High Similarity	NPD1511	Approved
0.8634	High Similarity	NPD7819	Suspended
0.8631	High Similarity	NPD7472	Approved
0.8623	High Similarity	NPD3818	Discontinued
0.8606	High Similarity	NPD6232	Discontinued
0.8588	High Similarity	NPD4338	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8544	High Similarity	NPD1512	Approved
0.8528	High Similarity	NPD4868	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7075	Discontinued
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8434	Intermediate Similarity	NPD6959	Discontinued
0.8421	Intermediate Similarity	NPD7251	Discontinued
0.8405	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8372	Intermediate Similarity	NPD7808	Phase 3
0.8363	Intermediate Similarity	NPD6797	Phase 2
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1549	Phase 2
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2534	Approved
0.8137	Intermediate Similarity	NPD2533	Approved
0.8137	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.8107	Intermediate Similarity	NPD1247	Approved
0.809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2796	Approved
0.7963	Intermediate Similarity	NPD6799	Approved
0.7937	Intermediate Similarity	NPD2800	Approved
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1613	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7874	Intermediate Similarity	NPD7228	Approved
0.787	Intermediate Similarity	NPD7768	Phase 2
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3749	Approved
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7799	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD37	Approved
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD3751	Discontinued
0.7765	Intermediate Similarity	NPD4967	Phase 2
0.7765	Intermediate Similarity	NPD4965	Approved
0.7765	Intermediate Similarity	NPD4966	Approved
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7746	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3226	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7702	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7688	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5710	Approved
0.7644	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD7390	Discontinued
0.7607	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7605	Intermediate Similarity	NPD5403	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7565	Intermediate Similarity	NPD8151	Discontinued
0.7562	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.756	Intermediate Similarity	NPD1653	Approved
0.7556	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7487	Intermediate Similarity	NPD7698	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD5401	Approved
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7469	Intermediate Similarity	NPD3748	Approved
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7870	Phase 2
0.7448	Intermediate Similarity	NPD7871	Phase 2
0.7444	Intermediate Similarity	NPD5953	Discontinued
0.7443	Intermediate Similarity	NPD7229	Phase 3
0.7435	Intermediate Similarity	NPD6823	Phase 2
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6190	Approved
0.7403	Intermediate Similarity	NPD7240	Approved
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7394	Intermediate Similarity	NPD1243	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2344	Approved
0.7358	Intermediate Similarity	NPD4625	Phase 3
0.7349	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7874	Approved
0.7342	Intermediate Similarity	NPD9494	Approved
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.734	Intermediate Similarity	NPD6535	Approved
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD7801	Approved
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7284	Intermediate Similarity	NPD1933	Approved
0.7283	Intermediate Similarity	NPD6844	Discontinued
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7207	Intermediate Similarity	NPD5242	Approved
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD5353	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7584	Approved
0.7189	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7126	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7458	Discontinued
0.7107	Intermediate Similarity	NPD1470	Approved
0.7105	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6212	Phase 3
0.7105	Intermediate Similarity	NPD6213	Phase 3
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8127	Discontinued
0.7081	Intermediate Similarity	NPD6832	Phase 2
0.7073	Intermediate Similarity	NPD7907	Approved
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD1201	Approved
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7045	Intermediate Similarity	NPD5761	Phase 2
0.7045	Intermediate Similarity	NPD5760	Phase 2
0.7029	Intermediate Similarity	NPD6386	Approved
0.7029	Intermediate Similarity	NPD6385	Approved
0.7026	Intermediate Similarity	NPD2494	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7006	Intermediate Similarity	NPD5408	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