NPASS Compound

Structure

NPC473720 OpenBabel07101718322D 38 44 0 0 1 0 0 0 0 0999 V2000 -6.7137 3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5272 5.2271 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9559 5.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 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 1.0000 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 4.1045 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 -6.1260 4.2091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5327 5.1226 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 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 3.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5437 4.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9449 5.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0103 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 4.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3516 6.8452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0103 4.3090 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 -4.9504 5.8271 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 -2.5981 5.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 16 1 0 0 0 0 4 27 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 2 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 12 14 1 0 0 0 0 13 24 1 0 0 0 0 14 1 1 6 0 0 0 14 15 1 0 0 0 0 15 2 1 1 0 0 0 15 25 1 0 0 0 0 16 31 2 0 0 0 0 16 35 1 0 0 0 0 17 13 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 27 1 6 0 0 0 19 29 1 6 0 0 0 20 28 1 6 0 0 0 20 29 1 0 0 0 0 21 27 1 0 0 0 0 21 32 2 0 0 0 0 22 30 1 6 0 0 0 22 35 1 0 0 0 0 23 12 1 1 0 0 0 23 28 1 0 0 0 0 23 36 1 0 0 0 0 24 30 1 1 0 0 0 24 37 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 0 0 0 0 26 34 2 0 0 0 0 26 38 1 0 0 0 0 27 30 1 6 0 0 0 28 5 1 1 0 0 0 28 38 1 0 0 0 0 29 11 1 1 0 0 0 30 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.26
Volume:	524.68
LogP:	3.386
LogD:	2.871
LogS:	-4.947
# Rotatable Bonds:	3
TPSA:	108.5
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	6.518
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.104
MDCK Permeability:	6.313637277344242e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	56.184654235839844%
Volume Distribution (VD):	0.662
Pgp-substrate:	42.40098571777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.237
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.81
CYP3A4-substrate:	0.753

ADMET: Excretion

Clearance (CL):	8.517
Half-life (T1/2):	0.579

ADMET: Toxicity

hERG Blockers:	0.531
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.735
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.952
Carcinogencity:	0.598
Eye Corrosion:	0.254
Eye Irritation:	0.163
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC473720

Natural Product ID:	NPC473720
*Common Name:**	DVACOXZKKLKNOU-MLYBQYODSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DVACOXZKKLKNOU-MLYBQYODSA-N
Standard InCHI:	InChI=1S/C30H38O8/c1-14-12-23(36-25(33)15(14)2)28(5)20-7-6-19-17-13-24-30(37-24)22(35-16(3)31)9-8-21(32)27(30,4)18(17)10-11-29(19,20)26(34)38-28/h8-9,14-15,17-20,22-24H,6-7,10-13H2,1-5H3/t14-,15+,17+,18-,19-,20+,22-,23+,24+,27-,28+,29+,30+/m0/s1
SMILES:	CC1CC(OC(=O)C1C)C2(C3CCC4C3(CCC5C4CC6C7(C5(C(=O)C=CC7OC(=O)C)C)O6)C(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450197
PubChem CID:	21670296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO1978	Dunalia brachyacantha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421731]
NPO1978	Dunalia brachyacantha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO1978	Dunalia brachyacantha	Species	Solanaceae	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	1
Others	4

Activity Type	# Activity
Individual Protein	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	<	0.28	uM	PMID[548800]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	<	0.28	uM	PMID[548800]
NPT2	Others	Unspecified		Ratio	>	1.5	n.a.	PMID[548800]
NPT27	Others	Unspecified		IC50	=	420.0	nM	PMID[548800]

☑ 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 NPC473720 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	302
0.1-0.2	1721
0.2-0.3	4912
0.3-0.4	8478
0.4-0.5	12530
0.5-0.6	6708
0.6-0.7	6140
0.7-0.8	1763
0.8-0.85	102
0.85-0.9	37
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC475520
0.9231	High Similarity	NPC473620
0.9138	High Similarity	NPC8369
0.8983	High Similarity	NPC287423
0.8966	High Similarity	NPC170538
0.8919	High Similarity	NPC470960
0.8898	High Similarity	NPC473635
0.8889	High Similarity	NPC469789
0.8889	High Similarity	NPC11895
0.887	High Similarity	NPC476960
0.8803	High Similarity	NPC23786
0.8803	High Similarity	NPC470265
0.8772	High Similarity	NPC270929
0.8739	High Similarity	NPC293112
0.8729	High Similarity	NPC120724
0.8729	High Similarity	NPC204812
0.8718	High Similarity	NPC204731
0.8718	High Similarity	NPC67569
0.8707	High Similarity	NPC473203
0.8678	High Similarity	NPC470880
0.8667	High Similarity	NPC42399
0.8667	High Similarity	NPC473253
0.8661	High Similarity	NPC253906
0.8655	High Similarity	NPC32868
0.8655	High Similarity	NPC172154
0.8655	High Similarity	NPC241456
0.8655	High Similarity	NPC81736
0.8632	High Similarity	NPC476961
0.8621	High Similarity	NPC329736
0.8621	High Similarity	NPC470420
0.8571	High Similarity	NPC474242
0.8547	High Similarity	NPC61520
0.8547	High Similarity	NPC42673
0.8534	High Similarity	NPC140055
0.8534	High Similarity	NPC286528
0.8534	High Similarity	NPC20302
0.8534	High Similarity	NPC167606
0.8525	High Similarity	NPC231529
0.8525	High Similarity	NPC473593
0.8512	High Similarity	NPC470882
0.8512	High Similarity	NPC473265
0.8475	Intermediate Similarity	NPC476962
0.8468	Intermediate Similarity	NPC470979
0.8468	Intermediate Similarity	NPC103088
0.8468	Intermediate Similarity	NPC470975
0.8462	Intermediate Similarity	NPC50774
0.8462	Intermediate Similarity	NPC709
0.8435	Intermediate Similarity	NPC122056
0.8421	Intermediate Similarity	NPC470246
0.8407	Intermediate Similarity	NPC469370
0.839	Intermediate Similarity	NPC264954
0.8387	Intermediate Similarity	NPC231240
0.8376	Intermediate Similarity	NPC183580
0.8376	Intermediate Similarity	NPC476965
0.8376	Intermediate Similarity	NPC470493
0.8376	Intermediate Similarity	NPC470492
0.8376	Intermediate Similarity	NPC312824
0.8376	Intermediate Similarity	NPC470959
0.8362	Intermediate Similarity	NPC470953
0.8362	Intermediate Similarity	NPC474181
0.8361	Intermediate Similarity	NPC305496
0.8361	Intermediate Similarity	NPC298841
0.8348	Intermediate Similarity	NPC265391
0.8348	Intermediate Similarity	NPC269530
0.8347	Intermediate Similarity	NPC8374
0.8347	Intermediate Similarity	NPC473255
0.8333	Intermediate Similarity	NPC269642
0.832	Intermediate Similarity	NPC316915
0.8319	Intermediate Similarity	NPC474370
0.8319	Intermediate Similarity	NPC251226
0.8319	Intermediate Similarity	NPC4548
0.8319	Intermediate Similarity	NPC474585
0.8293	Intermediate Similarity	NPC311534
0.8291	Intermediate Similarity	NPC243981
0.8288	Intermediate Similarity	NPC254202
0.8276	Intermediate Similarity	NPC25909
0.8276	Intermediate Similarity	NPC470120
0.825	Intermediate Similarity	NPC4021
0.825	Intermediate Similarity	NPC310511
0.825	Intermediate Similarity	NPC159456
0.825	Intermediate Similarity	NPC46570
0.8235	Intermediate Similarity	NPC230513
0.8235	Intermediate Similarity	NPC5292
0.823	Intermediate Similarity	NPC180744
0.8226	Intermediate Similarity	NPC476966
0.822	Intermediate Similarity	NPC239273
0.822	Intermediate Similarity	NPC469684
0.822	Intermediate Similarity	NPC284068
0.822	Intermediate Similarity	NPC476959
0.8214	Intermediate Similarity	NPC189616
0.8205	Intermediate Similarity	NPC238667
0.8205	Intermediate Similarity	NPC147912
0.8205	Intermediate Similarity	NPC67259
0.8197	Intermediate Similarity	NPC24651
0.8197	Intermediate Similarity	NPC3381
0.8197	Intermediate Similarity	NPC470922
0.8182	Intermediate Similarity	NPC153700
0.8182	Intermediate Similarity	NPC88326
0.8182	Intermediate Similarity	NPC107493
0.8167	Intermediate Similarity	NPC154491
0.8167	Intermediate Similarity	NPC143755
0.8167	Intermediate Similarity	NPC268530
0.8151	Intermediate Similarity	NPC113448
0.8151	Intermediate Similarity	NPC153440
0.8145	Intermediate Similarity	NPC245094
0.8136	Intermediate Similarity	NPC190286
0.8136	Intermediate Similarity	NPC476963
0.8136	Intermediate Similarity	NPC477509
0.8136	Intermediate Similarity	NPC470793
0.8125	Intermediate Similarity	NPC470954
0.8115	Intermediate Similarity	NPC473979
0.8115	Intermediate Similarity	NPC91693
0.8115	Intermediate Similarity	NPC18945
0.8115	Intermediate Similarity	NPC265557
0.8115	Intermediate Similarity	NPC67251
0.8115	Intermediate Similarity	NPC105926
0.8103	Intermediate Similarity	NPC474229
0.8095	Intermediate Similarity	NPC471855
0.8091	Intermediate Similarity	NPC252295
0.8091	Intermediate Similarity	NPC471932
0.8083	Intermediate Similarity	NPC77689
0.8083	Intermediate Similarity	NPC475775
0.8083	Intermediate Similarity	NPC475041
0.8083	Intermediate Similarity	NPC473274
0.8083	Intermediate Similarity	NPC476529
0.8083	Intermediate Similarity	NPC473636
0.8083	Intermediate Similarity	NPC472667
0.808	Intermediate Similarity	NPC35109
0.8073	Intermediate Similarity	NPC111684
0.8073	Intermediate Similarity	NPC58052
0.807	Intermediate Similarity	NPC476958
0.8067	Intermediate Similarity	NPC134430
0.8067	Intermediate Similarity	NPC473656
0.8067	Intermediate Similarity	NPC474518
0.8067	Intermediate Similarity	NPC473968
0.8067	Intermediate Similarity	NPC243065
0.8053	Intermediate Similarity	NPC164835
0.8053	Intermediate Similarity	NPC228669
0.8051	Intermediate Similarity	NPC284915
0.8049	Intermediate Similarity	NPC476729
0.8049	Intermediate Similarity	NPC470494
0.8049	Intermediate Similarity	NPC469790
0.8034	Intermediate Similarity	NPC277769
0.8034	Intermediate Similarity	NPC471933
0.8033	Intermediate Similarity	NPC312833
0.8017	Intermediate Similarity	NPC241192
0.8017	Intermediate Similarity	NPC107338
0.8017	Intermediate Similarity	NPC79579
0.8017	Intermediate Similarity	NPC5284
0.8017	Intermediate Similarity	NPC109607
0.8017	Intermediate Similarity	NPC473627
0.8016	Intermediate Similarity	NPC196921
0.8016	Intermediate Similarity	NPC220757
0.8016	Intermediate Similarity	NPC173347
0.8016	Intermediate Similarity	NPC476852
0.8	Intermediate Similarity	NPC189075
0.8	Intermediate Similarity	NPC186525
0.8	Intermediate Similarity	NPC275539
0.8	Intermediate Similarity	NPC311554
0.8	Intermediate Similarity	NPC257457
0.8	Intermediate Similarity	NPC284707
0.8	Intermediate Similarity	NPC475372
0.8	Intermediate Similarity	NPC292133
0.8	Intermediate Similarity	NPC473888
0.7984	Intermediate Similarity	NPC47113
0.7984	Intermediate Similarity	NPC120994
0.7984	Intermediate Similarity	NPC181999
0.7984	Intermediate Similarity	NPC203702
0.7984	Intermediate Similarity	NPC174367
0.7983	Intermediate Similarity	NPC270478
0.7983	Intermediate Similarity	NPC176840
0.7983	Intermediate Similarity	NPC266728
0.7983	Intermediate Similarity	NPC49492
0.7983	Intermediate Similarity	NPC148458
0.7982	Intermediate Similarity	NPC96377
0.7969	Intermediate Similarity	NPC471234
0.7966	Intermediate Similarity	NPC473535
0.7966	Intermediate Similarity	NPC477126
0.7966	Intermediate Similarity	NPC471627
0.7966	Intermediate Similarity	NPC159333
0.7966	Intermediate Similarity	NPC471173
0.7966	Intermediate Similarity	NPC52634
0.7965	Intermediate Similarity	NPC36688
0.7953	Intermediate Similarity	NPC34963
0.7951	Intermediate Similarity	NPC470878
0.7951	Intermediate Similarity	NPC473256
0.7951	Intermediate Similarity	NPC477046
0.7951	Intermediate Similarity	NPC470779
0.7951	Intermediate Similarity	NPC102822
0.7949	Intermediate Similarity	NPC469655
0.7949	Intermediate Similarity	NPC474315
0.7949	Intermediate Similarity	NPC469656
0.7949	Intermediate Similarity	NPC474846
0.7946	Intermediate Similarity	NPC310981
0.7937	Intermediate Similarity	NPC175186
0.7937	Intermediate Similarity	NPC476851
0.7937	Intermediate Similarity	NPC221414
0.7937	Intermediate Similarity	NPC471407
0.7934	Intermediate Similarity	NPC473839
0.7934	Intermediate Similarity	NPC470495

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 NPC473720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	1872
0.2-0.3	3891
0.3-0.4	2036
0.4-0.5	651
0.5-0.6	222
0.6-0.7	187
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8534	High Similarity	NPD7115	Discovery
0.8304	Intermediate Similarity	NPD6008	Approved
0.7795	Intermediate Similarity	NPD7319	Approved
0.776	Intermediate Similarity	NPD7492	Approved
0.7724	Intermediate Similarity	NPD6054	Approved
0.7724	Intermediate Similarity	NPD6319	Approved
0.7717	Intermediate Similarity	NPD7736	Approved
0.7698	Intermediate Similarity	NPD7507	Approved
0.7698	Intermediate Similarity	NPD6616	Approved
0.7638	Intermediate Similarity	NPD7078	Approved
0.7607	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6370	Approved
0.7583	Intermediate Similarity	NPD8297	Approved
0.752	Intermediate Similarity	NPD6016	Approved
0.752	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5988	Approved
0.744	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6881	Approved
0.7395	Intermediate Similarity	NPD6899	Approved
0.7395	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4632	Approved
0.7364	Intermediate Similarity	NPD8293	Discontinued
0.7339	Intermediate Similarity	NPD3573	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.7311	Intermediate Similarity	NPD5697	Approved
0.7304	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD7638	Approved
0.7295	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7266	Intermediate Similarity	NPD7604	Phase 2
0.725	Intermediate Similarity	NPD7320	Approved
0.7241	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD7639	Approved
0.7227	Intermediate Similarity	NPD5739	Approved
0.7227	Intermediate Similarity	NPD6402	Approved
0.7227	Intermediate Similarity	NPD7128	Approved
0.7227	Intermediate Similarity	NPD6675	Approved
0.7213	Intermediate Similarity	NPD6869	Approved
0.7213	Intermediate Similarity	NPD6847	Approved
0.7213	Intermediate Similarity	NPD6617	Approved
0.7213	Intermediate Similarity	NPD8130	Phase 1
0.72	Intermediate Similarity	NPD6009	Approved
0.719	Intermediate Similarity	NPD6013	Approved
0.719	Intermediate Similarity	NPD6012	Approved
0.719	Intermediate Similarity	NPD6014	Approved
0.719	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD7327	Approved
0.7132	Intermediate Similarity	NPD8328	Phase 3
0.7131	Intermediate Similarity	NPD4634	Approved
0.7109	Intermediate Similarity	NPD8513	Phase 3
0.7109	Intermediate Similarity	NPD7503	Approved
0.7109	Intermediate Similarity	NPD8033	Approved
0.7109	Intermediate Similarity	NPD5983	Phase 2
0.7109	Intermediate Similarity	NPD8517	Approved
0.7109	Intermediate Similarity	NPD8515	Approved
0.7109	Intermediate Similarity	NPD8516	Approved
0.7107	Intermediate Similarity	NPD6011	Approved
0.7107	Intermediate Similarity	NPD6686	Approved
0.7105	Intermediate Similarity	NPD6001	Approved
0.7087	Intermediate Similarity	NPD7516	Approved
0.708	Intermediate Similarity	NPD6079	Approved
0.7031	Intermediate Similarity	NPD8377	Approved
0.7031	Intermediate Similarity	NPD8294	Approved
0.7025	Intermediate Similarity	NPD5701	Approved
0.7023	Intermediate Similarity	NPD6336	Discontinued
0.7018	Intermediate Similarity	NPD6399	Phase 3
0.7016	Intermediate Similarity	NPD6053	Discontinued
0.7015	Intermediate Similarity	NPD7260	Phase 2
0.6977	Remote Similarity	NPD8380	Approved
0.6977	Remote Similarity	NPD8379	Approved
0.6977	Remote Similarity	NPD8335	Approved
0.6977	Remote Similarity	NPD8296	Approved
0.6977	Remote Similarity	NPD8378	Approved
0.6975	Remote Similarity	NPD5211	Phase 2
0.6964	Remote Similarity	NPD5737	Approved
0.6964	Remote Similarity	NPD6903	Approved
0.6964	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6672	Approved
0.6957	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD4696	Approved
0.6949	Remote Similarity	NPD5286	Approved
0.6937	Remote Similarity	NPD7521	Approved
0.6937	Remote Similarity	NPD6684	Approved
0.6937	Remote Similarity	NPD6409	Approved
0.6937	Remote Similarity	NPD7334	Approved
0.6937	Remote Similarity	NPD7146	Approved
0.6937	Remote Similarity	NPD5330	Approved
0.693	Remote Similarity	NPD5693	Phase 1
0.6917	Remote Similarity	NPD6033	Approved
0.6903	Remote Similarity	NPD5328	Approved
0.6885	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6412	Phase 2
0.686	Remote Similarity	NPD5141	Approved
0.6855	Remote Similarity	NPD6371	Approved
0.6847	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6921	Approved
0.6846	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5207	Approved
0.6838	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5221	Approved
0.6838	Remote Similarity	NPD5222	Approved
0.6838	Remote Similarity	NPD6845	Suspended
0.6833	Remote Similarity	NPD5224	Approved
0.6833	Remote Similarity	NPD5226	Approved
0.6833	Remote Similarity	NPD4633	Approved
0.6833	Remote Similarity	NPD5225	Approved
0.6822	Remote Similarity	NPD7100	Approved
0.6822	Remote Similarity	NPD7101	Approved
0.681	Remote Similarity	NPD7748	Approved
0.68	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6083	Phase 2
0.678	Remote Similarity	NPD4755	Approved
0.678	Remote Similarity	NPD6084	Phase 2
0.678	Remote Similarity	NPD5173	Approved
0.678	Remote Similarity	NPD7902	Approved
0.6777	Remote Similarity	NPD5175	Approved
0.6777	Remote Similarity	NPD5174	Approved
0.6754	Remote Similarity	NPD6080	Approved
0.6754	Remote Similarity	NPD6904	Approved
0.6754	Remote Similarity	NPD6673	Approved
0.6754	Remote Similarity	NPD1695	Approved
0.6752	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5223	Approved
0.6744	Remote Similarity	NPD6335	Approved
0.6727	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5696	Approved
0.6719	Remote Similarity	NPD6274	Approved
0.6719	Remote Similarity	NPD6868	Approved
0.6716	Remote Similarity	NPD8074	Phase 3
0.6696	Remote Similarity	NPD6698	Approved
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD5785	Approved
0.6695	Remote Similarity	NPD4697	Phase 3
0.6694	Remote Similarity	NPD4729	Approved
0.6694	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD4730	Approved
0.6693	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.664	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7515	Phase 2
0.6638	Remote Similarity	NPD6411	Approved
0.6637	Remote Similarity	NPD3618	Phase 1
0.6637	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6314	Approved
0.6615	Remote Similarity	NPD6313	Approved
0.6612	Remote Similarity	NPD5344	Discontinued
0.661	Remote Similarity	NPD5695	Phase 3
0.6609	Remote Similarity	NPD6051	Approved
0.6587	Remote Similarity	NPD5248	Approved
0.6587	Remote Similarity	NPD5247	Approved
0.6587	Remote Similarity	NPD5249	Phase 3
0.6587	Remote Similarity	NPD5251	Approved
0.6587	Remote Similarity	NPD5250	Approved
0.6581	Remote Similarity	NPD5779	Approved
0.6581	Remote Similarity	NPD5778	Approved
0.6532	Remote Similarity	NPD4767	Approved
0.6532	Remote Similarity	NPD4768	Approved
0.6525	Remote Similarity	NPD5282	Discontinued
0.6522	Remote Similarity	NPD5208	Approved
0.6504	Remote Similarity	NPD6052	Approved
0.6496	Remote Similarity	NPD7637	Suspended
0.6496	Remote Similarity	NPD5694	Approved
0.6496	Remote Similarity	NPD8034	Phase 2
0.6496	Remote Similarity	NPD8035	Phase 2
0.6496	Remote Similarity	NPD6050	Approved
0.6491	Remote Similarity	NPD6098	Approved
0.6475	Remote Similarity	NPD8338	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6101	Approved
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.646	Remote Similarity	NPD7799	Discontinued
0.646	Remote Similarity	NPD4786	Approved
0.6449	Remote Similarity	NPD5956	Approved
0.6441	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD5128	Approved
0.6423	Remote Similarity	NPD8337	Approved
0.6423	Remote Similarity	NPD8336	Approved
0.641	Remote Similarity	NPD5692	Phase 3
0.6406	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5216	Approved
0.6406	Remote Similarity	NPD5217	Approved
0.6406	Remote Similarity	NPD5215	Approved
0.6371	Remote Similarity	NPD4754	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