NPASS Compound

Structure

NPC475520 OpenBabel07101718222D 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 0 0 0 0 0 0 0 0 0 0 -6.5327 5.1226 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 -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 1 14 1 0 0 0 0 2 15 1 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 15 2 0 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:	524.24
Volume:	522.044
LogP:	3.203
LogD:	2.133
LogS:	-4.941
# 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:	0.232
Synthetic Accessibility Score:	6.528
Fsp3:	0.733
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:	-5.146
MDCK Permeability:	4.6565277443733066e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	53.462135314941406%
Volume Distribution (VD):	0.826
Pgp-substrate:	52.88337326049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.775
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	7.327
Half-life (T1/2):	0.603

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.905
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.901
Maximum Recommended Daily Dose:	0.67
Skin Sensitization:	0.784
Carcinogencity:	0.123
Eye Corrosion:	0.012
Eye Irritation:	0.099
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC475520

Natural Product ID:	NPC475520
*Common Name:**	IEABCZXUVAYIAD-OAZABPQTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IEABCZXUVAYIAD-OAZABPQTSA-N
Standard InCHI:	InChI=1S/C30H36O8/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/h8-9,17-20,22-24H,6-7,10-13H2,1-5H3/t17-,18+,19+,20-,22+,23-,24-,27+,28-,29-,30-/m1/s1
SMILES:	CC1=C(C(=O)OC(C1)C2(C3CCC4C3(CCC5C4CC6C7(C5(C(=O)C=CC7OC(=O)C)C)O6)C(=O)O2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507201
PubChem CID:	21670297
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	<	0.29	uM	PMID[469339]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	<	0.29	uM	PMID[469339]
NPT2	Others	Unspecified		Ratio	>	2.0	n.a.	PMID[469339]
NPT27	Others	Unspecified		IC50	=	570.0	nM	PMID[469339]

☑ 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 NPC475520 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	1628
0.2-0.3	4635
0.3-0.4	8152
0.4-0.5	12818
0.5-0.6	6928
0.6-0.7	6282
0.7-0.8	1751
0.8-0.85	147
0.85-0.9	51
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC473720
0.9391	High Similarity	NPC8369
0.9217	High Similarity	NPC170538
0.9145	High Similarity	NPC473635
0.9138	High Similarity	NPC469789
0.9138	High Similarity	NPC11895
0.9052	High Similarity	NPC23786
0.9052	High Similarity	NPC470265
0.8992	High Similarity	NPC473620
0.8983	High Similarity	NPC293112
0.8966	High Similarity	NPC67569
0.8908	High Similarity	NPC287423
0.8898	High Similarity	NPC81736
0.8898	High Similarity	NPC172154
0.8839	High Similarity	NPC470960
0.8814	High Similarity	NPC204812
0.8814	High Similarity	NPC120724
0.8803	High Similarity	NPC204731
0.8793	High Similarity	NPC42673
0.8793	High Similarity	NPC476960
0.8783	High Similarity	NPC286528
0.8783	High Similarity	NPC20302
0.8783	High Similarity	NPC140055
0.8783	High Similarity	NPC167606
0.876	High Similarity	NPC473593
0.875	High Similarity	NPC253906
0.875	High Similarity	NPC42399
0.8739	High Similarity	NPC241456
0.8739	High Similarity	NPC32868
0.8707	High Similarity	NPC470420
0.8707	High Similarity	NPC709
0.8707	High Similarity	NPC50774
0.8684	High Similarity	NPC122056
0.8661	High Similarity	NPC469370
0.8632	High Similarity	NPC264954
0.8621	High Similarity	NPC312824
0.8621	High Similarity	NPC470493
0.8621	High Similarity	NPC183580
0.8621	High Similarity	NPC470492
0.8609	High Similarity	NPC474181
0.8607	High Similarity	NPC231529
0.8583	High Similarity	NPC8374
0.8571	High Similarity	NPC269642
0.8559	High Similarity	NPC103088
0.8559	High Similarity	NPC470979
0.8559	High Similarity	NPC470975
0.8559	High Similarity	NPC251226
0.8559	High Similarity	NPC474585
0.8559	High Similarity	NPC476961
0.8559	High Similarity	NPC474370
0.8534	High Similarity	NPC270929
0.8522	High Similarity	NPC25909
0.8487	Intermediate Similarity	NPC4021
0.8487	Intermediate Similarity	NPC46570
0.8487	Intermediate Similarity	NPC159456
0.8482	Intermediate Similarity	NPC180744
0.8475	Intermediate Similarity	NPC5292
0.8475	Intermediate Similarity	NPC473203
0.8475	Intermediate Similarity	NPC230513
0.8468	Intermediate Similarity	NPC231240
0.8462	Intermediate Similarity	NPC469684
0.8455	Intermediate Similarity	NPC470880
0.8448	Intermediate Similarity	NPC67259
0.8448	Intermediate Similarity	NPC147912
0.8443	Intermediate Similarity	NPC473253
0.8443	Intermediate Similarity	NPC298841
0.8435	Intermediate Similarity	NPC269530
0.843	Intermediate Similarity	NPC3381
0.8417	Intermediate Similarity	NPC88326
0.8417	Intermediate Similarity	NPC153700
0.8417	Intermediate Similarity	NPC107493
0.8403	Intermediate Similarity	NPC4548
0.8403	Intermediate Similarity	NPC476962
0.8403	Intermediate Similarity	NPC268530
0.8403	Intermediate Similarity	NPC154491
0.84	Intermediate Similarity	NPC316915
0.839	Intermediate Similarity	NPC153440
0.839	Intermediate Similarity	NPC329736
0.8378	Intermediate Similarity	NPC254202
0.8376	Intermediate Similarity	NPC243981
0.8376	Intermediate Similarity	NPC190286
0.8362	Intermediate Similarity	NPC470120
0.8333	Intermediate Similarity	NPC310511
0.8333	Intermediate Similarity	NPC474242
0.8319	Intermediate Similarity	NPC61520
0.8319	Intermediate Similarity	NPC473274
0.8319	Intermediate Similarity	NPC475041
0.8306	Intermediate Similarity	NPC476966
0.8305	Intermediate Similarity	NPC239273
0.8305	Intermediate Similarity	NPC243065
0.8305	Intermediate Similarity	NPC473656
0.8305	Intermediate Similarity	NPC470959
0.8305	Intermediate Similarity	NPC284068
0.8305	Intermediate Similarity	NPC476965
0.8304	Intermediate Similarity	NPC189616
0.8293	Intermediate Similarity	NPC470882
0.8293	Intermediate Similarity	NPC473265
0.8291	Intermediate Similarity	NPC470953
0.8291	Intermediate Similarity	NPC238667
0.8291	Intermediate Similarity	NPC284915
0.8279	Intermediate Similarity	NPC470494
0.8279	Intermediate Similarity	NPC469790
0.8276	Intermediate Similarity	NPC265391
0.8261	Intermediate Similarity	NPC473627
0.825	Intermediate Similarity	NPC79579
0.825	Intermediate Similarity	NPC143755
0.8235	Intermediate Similarity	NPC284707
0.8235	Intermediate Similarity	NPC475372
0.8235	Intermediate Similarity	NPC113448
0.8235	Intermediate Similarity	NPC186525
0.8226	Intermediate Similarity	NPC245094
0.8226	Intermediate Similarity	NPC311534
0.822	Intermediate Similarity	NPC477509
0.822	Intermediate Similarity	NPC470793
0.822	Intermediate Similarity	NPC176840
0.8211	Intermediate Similarity	NPC203702
0.8211	Intermediate Similarity	NPC120994
0.8205	Intermediate Similarity	NPC473535
0.8198	Intermediate Similarity	NPC310981
0.8197	Intermediate Similarity	NPC473979
0.819	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC474315
0.819	Intermediate Similarity	NPC474229
0.819	Intermediate Similarity	NPC470246
0.819	Intermediate Similarity	NPC469655
0.819	Intermediate Similarity	NPC469656
0.8182	Intermediate Similarity	NPC471932
0.8182	Intermediate Similarity	NPC470878
0.8182	Intermediate Similarity	NPC252295
0.8182	Intermediate Similarity	NPC473256
0.8167	Intermediate Similarity	NPC473636
0.8167	Intermediate Similarity	NPC312536
0.8167	Intermediate Similarity	NPC77689
0.8167	Intermediate Similarity	NPC305260
0.8167	Intermediate Similarity	NPC270850
0.8167	Intermediate Similarity	NPC470495
0.8167	Intermediate Similarity	NPC472667
0.816	Intermediate Similarity	NPC35109
0.816	Intermediate Similarity	NPC221414
0.8151	Intermediate Similarity	NPC98249
0.8151	Intermediate Similarity	NPC53396
0.8151	Intermediate Similarity	NPC476959
0.8151	Intermediate Similarity	NPC58662
0.8151	Intermediate Similarity	NPC55296
0.8151	Intermediate Similarity	NPC134430
0.8151	Intermediate Similarity	NPC474518
0.8145	Intermediate Similarity	NPC305496
0.8142	Intermediate Similarity	NPC228669
0.8142	Intermediate Similarity	NPC164835
0.813	Intermediate Similarity	NPC24651
0.813	Intermediate Similarity	NPC473255
0.813	Intermediate Similarity	NPC470922
0.812	Intermediate Similarity	NPC476163
0.812	Intermediate Similarity	NPC236217
0.812	Intermediate Similarity	NPC471933
0.812	Intermediate Similarity	NPC222834
0.812	Intermediate Similarity	NPC277769
0.8103	Intermediate Similarity	NPC5284
0.8103	Intermediate Similarity	NPC37116
0.8099	Intermediate Similarity	NPC241192
0.8095	Intermediate Similarity	NPC196921
0.8095	Intermediate Similarity	NPC220757
0.8095	Intermediate Similarity	NPC173347
0.8091	Intermediate Similarity	NPC292133
0.8087	Intermediate Similarity	NPC189075
0.8087	Intermediate Similarity	NPC275539
0.8083	Intermediate Similarity	NPC311554
0.8083	Intermediate Similarity	NPC475913
0.8083	Intermediate Similarity	NPC257457
0.8073	Intermediate Similarity	NPC281134
0.807	Intermediate Similarity	NPC96377
0.8067	Intermediate Similarity	NPC270478
0.8067	Intermediate Similarity	NPC49492
0.8067	Intermediate Similarity	NPC148458
0.8067	Intermediate Similarity	NPC476963
0.8067	Intermediate Similarity	NPC266728
0.8067	Intermediate Similarity	NPC470075
0.8053	Intermediate Similarity	NPC36688
0.8053	Intermediate Similarity	NPC470954
0.8051	Intermediate Similarity	NPC52634
0.8051	Intermediate Similarity	NPC159333
0.8051	Intermediate Similarity	NPC477126
0.8049	Intermediate Similarity	NPC67251
0.8049	Intermediate Similarity	NPC91693
0.8049	Intermediate Similarity	NPC265557
0.8049	Intermediate Similarity	NPC105926
0.8049	Intermediate Similarity	NPC18945
0.8049	Intermediate Similarity	NPC6193
0.8049	Intermediate Similarity	NPC55602
0.8031	Intermediate Similarity	NPC471855
0.8031	Intermediate Similarity	NPC34963
0.8017	Intermediate Similarity	NPC475834
0.8017	Intermediate Similarity	NPC473839
0.8017	Intermediate Similarity	NPC474179
0.8017	Intermediate Similarity	NPC211093
0.8017	Intermediate Similarity	NPC476529
0.8017	Intermediate Similarity	NPC475775
0.8017	Intermediate Similarity	NPC472933
0.8017	Intermediate Similarity	NPC112457
0.8017	Intermediate Similarity	NPC471934

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 NPC475520 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	1748
0.2-0.3	3838
0.3-0.4	2138
0.4-0.5	728
0.5-0.6	223
0.6-0.7	169
0.7-0.8	56
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8783	High Similarity	NPD7115	Discovery
0.8393	Intermediate Similarity	NPD6008	Approved
0.784	Intermediate Similarity	NPD7492	Approved
0.7805	Intermediate Similarity	NPD6054	Approved
0.7805	Intermediate Similarity	NPD6319	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD6616	Approved
0.7734	Intermediate Similarity	NPD7319	Approved
0.7717	Intermediate Similarity	NPD7078	Approved
0.7692	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6370	Approved
0.7667	Intermediate Similarity	NPD8297	Approved
0.7638	Intermediate Similarity	NPD7507	Approved
0.76	Intermediate Similarity	NPD6015	Approved
0.76	Intermediate Similarity	NPD6016	Approved
0.7589	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD6649	Approved
0.7583	Intermediate Similarity	NPD6650	Approved
0.754	Intermediate Similarity	NPD5988	Approved
0.752	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6881	Approved
0.7479	Intermediate Similarity	NPD6899	Approved
0.7459	Intermediate Similarity	NPD4632	Approved
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.7417	Intermediate Similarity	NPD6372	Approved
0.7417	Intermediate Similarity	NPD6373	Approved
0.7395	Intermediate Similarity	NPD5697	Approved
0.7391	Intermediate Similarity	NPD4225	Approved
0.7391	Intermediate Similarity	NPD7638	Approved
0.7377	Intermediate Similarity	NPD6882	Approved
0.7355	Intermediate Similarity	NPD6883	Approved
0.7355	Intermediate Similarity	NPD7102	Approved
0.7355	Intermediate Similarity	NPD7290	Approved
0.7344	Intermediate Similarity	NPD7604	Phase 2
0.7333	Intermediate Similarity	NPD7320	Approved
0.7328	Intermediate Similarity	NPD7640	Approved
0.7328	Intermediate Similarity	NPD7639	Approved
0.7311	Intermediate Similarity	NPD7128	Approved
0.7311	Intermediate Similarity	NPD5739	Approved
0.7311	Intermediate Similarity	NPD6675	Approved
0.7311	Intermediate Similarity	NPD6402	Approved
0.7295	Intermediate Similarity	NPD6869	Approved
0.7295	Intermediate Similarity	NPD6847	Approved
0.7295	Intermediate Similarity	NPD8130	Phase 1
0.7295	Intermediate Similarity	NPD6617	Approved
0.728	Intermediate Similarity	NPD6009	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6013	Approved
0.7248	Intermediate Similarity	NPD1694	Approved
0.7236	Intermediate Similarity	NPD6053	Discontinued
0.7213	Intermediate Similarity	NPD4634	Approved
0.7193	Intermediate Similarity	NPD6001	Approved
0.719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6011	Approved
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7188	Intermediate Similarity	NPD7503	Approved
0.7188	Intermediate Similarity	NPD5983	Phase 2
0.7168	Intermediate Similarity	NPD6079	Approved
0.7107	Intermediate Similarity	NPD5701	Approved
0.7105	Intermediate Similarity	NPD6399	Phase 3
0.7099	Intermediate Similarity	NPD6336	Discontinued
0.7087	Intermediate Similarity	NPD7328	Approved
0.7087	Intermediate Similarity	NPD7327	Approved
0.7077	Intermediate Similarity	NPD8328	Phase 3
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7054	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD8033	Approved
0.7054	Intermediate Similarity	NPD8515	Approved
0.7054	Intermediate Similarity	NPD6672	Approved
0.7054	Intermediate Similarity	NPD8516	Approved
0.7054	Intermediate Similarity	NPD6903	Approved
0.7054	Intermediate Similarity	NPD5737	Approved
0.7054	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6686	Approved
0.7043	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7900	Approved
0.7034	Intermediate Similarity	NPD4696	Approved
0.7034	Intermediate Similarity	NPD5285	Approved
0.7034	Intermediate Similarity	NPD5286	Approved
0.7031	Intermediate Similarity	NPD7516	Approved
0.7027	Intermediate Similarity	NPD7334	Approved
0.7027	Intermediate Similarity	NPD5330	Approved
0.7027	Intermediate Similarity	NPD6409	Approved
0.7027	Intermediate Similarity	NPD6684	Approved
0.7027	Intermediate Similarity	NPD7521	Approved
0.7027	Intermediate Similarity	NPD7146	Approved
0.7018	Intermediate Similarity	NPD5693	Phase 1
0.6992	Remote Similarity	NPD6033	Approved
0.6991	Remote Similarity	NPD5328	Approved
0.6977	Remote Similarity	NPD8377	Approved
0.6977	Remote Similarity	NPD8294	Approved
0.6967	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7260	Phase 2
0.6942	Remote Similarity	NPD5141	Approved
0.6937	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6371	Approved
0.693	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD8378	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD8335	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8380	Approved
0.6923	Remote Similarity	NPD8379	Approved
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5222	Approved
0.6923	Remote Similarity	NPD8296	Approved
0.6917	Remote Similarity	NPD4633	Approved
0.6917	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD5225	Approved
0.6917	Remote Similarity	NPD5226	Approved
0.6899	Remote Similarity	NPD7101	Approved
0.6899	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD7748	Approved
0.688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5173	Approved
0.6864	Remote Similarity	NPD4755	Approved
0.6864	Remote Similarity	NPD7902	Approved
0.6864	Remote Similarity	NPD6083	Phase 2
0.6864	Remote Similarity	NPD6084	Phase 2
0.686	Remote Similarity	NPD5174	Approved
0.686	Remote Similarity	NPD5175	Approved
0.6842	Remote Similarity	NPD6080	Approved
0.6842	Remote Similarity	NPD6904	Approved
0.6842	Remote Similarity	NPD1695	Approved
0.6842	Remote Similarity	NPD6673	Approved
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5223	Approved
0.6829	Remote Similarity	NPD6412	Phase 2
0.6822	Remote Similarity	NPD6335	Approved
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5696	Approved
0.6797	Remote Similarity	NPD6274	Approved
0.6797	Remote Similarity	NPD6868	Approved
0.6788	Remote Similarity	NPD6845	Suspended
0.678	Remote Similarity	NPD4697	Phase 3
0.6777	Remote Similarity	NPD7632	Discontinued
0.6774	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4729	Approved
0.675	Remote Similarity	NPD6648	Approved
0.675	Remote Similarity	NPD4700	Approved
0.6744	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3618	Phase 1
0.6724	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD6051	Approved
0.6695	Remote Similarity	NPD5695	Phase 3
0.6694	Remote Similarity	NPD5344	Discontinued
0.6692	Remote Similarity	NPD6314	Approved
0.6692	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6641	Remote Similarity	NPD8133	Approved
0.6638	Remote Similarity	NPD6698	Approved
0.6638	Remote Similarity	NPD5785	Approved
0.6638	Remote Similarity	NPD46	Approved
0.6613	Remote Similarity	NPD4767	Approved
0.6613	Remote Similarity	NPD4768	Approved
0.6609	Remote Similarity	NPD5208	Approved
0.6587	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6052	Approved
0.6581	Remote Similarity	NPD8035	Phase 2
0.6581	Remote Similarity	NPD5694	Approved
0.6581	Remote Similarity	NPD6050	Approved
0.6581	Remote Similarity	NPD6411	Approved
0.6581	Remote Similarity	NPD7637	Suspended
0.6581	Remote Similarity	NPD8034	Phase 2
0.6579	Remote Similarity	NPD6098	Approved
0.6555	Remote Similarity	NPD5210	Approved
0.6555	Remote Similarity	NPD4629	Approved
0.6549	Remote Similarity	NPD4786	Approved
0.6541	Remote Similarity	NPD6908	Approved
0.6541	Remote Similarity	NPD6909	Approved
0.6525	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD7799	Discontinued
0.6522	Remote Similarity	NPD5956	Approved
0.6508	Remote Similarity	NPD5128	Approved
0.6496	Remote Similarity	NPD5692	Phase 3
0.6484	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5215	Approved
0.6484	Remote Similarity	NPD5217	Approved
0.6484	Remote Similarity	NPD5216	Approved
0.6471	Remote Similarity	NPD5282	Discontinued
0.6452	Remote Similarity	NPD4754	Approved
0.6444	Remote Similarity	NPD6067	Discontinued
0.6441	Remote Similarity	NPD5281	Approved
0.6441	Remote Similarity	NPD5284	Approved
0.6434	Remote Similarity	NPD6334	Approved
0.6434	Remote Similarity	NPD6333	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