NPASS Compound

Structure

NPC473238 OpenBabel07101718222D 35 39 0 0 1 0 0 0 0 0999 V2000 -6.5446 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9047 3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5848 6.2524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 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 -2.6831 -0.3090 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 -4.2793 3.4190 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 4.6051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2356 3.8349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 C 0 0 1 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 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 3 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 -5.4653 2.6488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7927 5.2742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 8 35 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 32 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 20 35 1 0 0 0 0 21 32 1 0 0 0 0 22 3 1 1 0 0 0 22 23 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 30 1 6 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 33 1 6 0 0 0 28 29 1 6 0 0 0 29 7 1 1 0 0 0 30 31 1 1 0 0 0 31 18 1 1 0 0 0 32 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.42
Volume:	545.616
LogP:	6.928
LogD:	5.278
LogS:	-5.532
# Rotatable Bonds:	7
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.702
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.086
MDCK Permeability:	2.0342862626421265e-05
Pgp-inhibitor:	0.281
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	96.32630157470703%
Volume Distribution (VD):	1.348
Pgp-substrate:	1.771176815032959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.482
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.353
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.677

ADMET: Excretion

Clearance (CL):	7.784
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.391
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.931
Carcinogencity:	0.062
Eye Corrosion:	0.008
Eye Irritation:	0.039
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC473238

Natural Product ID:	NPC473238
*Common Name:**	BGKDKAMMXBHXAE-YGBPDJJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BGKDKAMMXBHXAE-YGBPDJJZSA-N
Standard InCHI:	InChI=1S/C32H56O3/c1-21(2)32(34,20-35-8)16-11-22(3)23-12-14-29(7)25-10-9-24-27(4,5)26(33)13-15-30(24)19-31(25,30)18-17-28(23,29)6/h21-26,33-34H,9-20H2,1-8H3/t22-,23-,24+,25+,26+,28-,29+,30-,31+,32?/m1/s1
SMILES:	CC(C)C(CCC(C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C)(COC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376789
PubChem CID:	11641663
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO32928	glomerella fusarioides	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]

☑ 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	8

Activity Type	# Activity
Cell Line	1
Organism	7
Others	1

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[449569]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[449569]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	15.2	%	PMID[449569]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	65.4	%	PMID[449569]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	83.1	%	PMID[449569]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	6.7	nM	PMID[449569]
NPT2	Others	Unspecified		Activity	=	2.1	n.a.	PMID[449569]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	27.0	%	PMID[449569]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	87.0	%	PMID[449569]

☑ 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 NPC473238 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	408
0.1-0.2	4603
0.2-0.3	16723
0.3-0.4	8967
0.4-0.5	4744
0.5-0.6	4752
0.6-0.7	1918
0.7-0.8	446
0.8-0.85	99
0.85-0.9	25
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472341
0.9552	High Similarity	NPC470830
0.9552	High Similarity	NPC299948
0.9552	High Similarity	NPC241085
0.9028	High Similarity	NPC470145
0.9	High Similarity	NPC8004
0.9	High Similarity	NPC473279
0.9	High Similarity	NPC127283
0.9	High Similarity	NPC131506
0.9	High Similarity	NPC195530
0.9	High Similarity	NPC157777
0.8986	High Similarity	NPC107919
0.8971	High Similarity	NPC473230
0.8971	High Similarity	NPC475884
0.8955	High Similarity	NPC41577
0.8955	High Similarity	NPC473276
0.8955	High Similarity	NPC474380
0.8889	High Similarity	NPC270306
0.8889	High Similarity	NPC91387
0.8889	High Similarity	NPC231680
0.8857	High Similarity	NPC231945
0.8806	High Similarity	NPC69149
0.8696	High Similarity	NPC63190
0.8696	High Similarity	NPC48079
0.8657	High Similarity	NPC114891
0.8649	High Similarity	NPC474574
0.8649	High Similarity	NPC64081
0.8649	High Similarity	NPC11907
0.8649	High Similarity	NPC133596
0.8611	High Similarity	NPC153719
0.8592	High Similarity	NPC282454
0.8571	High Similarity	NPC475388
0.8571	High Similarity	NPC472741
0.8553	High Similarity	NPC16449
0.8551	High Similarity	NPC142712
0.8533	High Similarity	NPC147993
0.8507	High Similarity	NPC218585
0.8507	High Similarity	NPC148174
0.8507	High Similarity	NPC71460
0.8493	Intermediate Similarity	NPC10476
0.8493	Intermediate Similarity	NPC192501
0.8493	Intermediate Similarity	NPC228994
0.8472	Intermediate Similarity	NPC1340
0.8472	Intermediate Similarity	NPC187471
0.8472	Intermediate Similarity	NPC157422
0.8472	Intermediate Similarity	NPC470071
0.8472	Intermediate Similarity	NPC109457
0.8472	Intermediate Similarity	NPC252182
0.8472	Intermediate Similarity	NPC100586
0.8451	Intermediate Similarity	NPC129829
0.8451	Intermediate Similarity	NPC254037
0.8451	Intermediate Similarity	NPC66407
0.8421	Intermediate Similarity	NPC477282
0.8421	Intermediate Similarity	NPC287452
0.8421	Intermediate Similarity	NPC81074
0.8406	Intermediate Similarity	NPC190827
0.8406	Intermediate Similarity	NPC475943
0.8406	Intermediate Similarity	NPC243469
0.8406	Intermediate Similarity	NPC260116
0.8378	Intermediate Similarity	NPC158208
0.8378	Intermediate Similarity	NPC196136
0.8378	Intermediate Similarity	NPC317242
0.8378	Intermediate Similarity	NPC243027
0.8356	Intermediate Similarity	NPC470610
0.8333	Intermediate Similarity	NPC192192
0.8289	Intermediate Similarity	NPC471769
0.8286	Intermediate Similarity	NPC44122
0.8267	Intermediate Similarity	NPC163597
0.8267	Intermediate Similarity	NPC91573
0.8261	Intermediate Similarity	NPC159654
0.8261	Intermediate Similarity	NPC167995
0.8261	Intermediate Similarity	NPC281540
0.8261	Intermediate Similarity	NPC118937
0.8243	Intermediate Similarity	NPC48795
0.8243	Intermediate Similarity	NPC477508
0.8243	Intermediate Similarity	NPC478130
0.8235	Intermediate Similarity	NPC95804
0.8235	Intermediate Similarity	NPC185547
0.8228	Intermediate Similarity	NPC111582
0.8228	Intermediate Similarity	NPC477285
0.8219	Intermediate Similarity	NPC127094
0.8209	Intermediate Similarity	NPC95958
0.8205	Intermediate Similarity	NPC190940
0.8205	Intermediate Similarity	NPC12933
0.8194	Intermediate Similarity	NPC477820
0.8194	Intermediate Similarity	NPC99264
0.8158	Intermediate Similarity	NPC185915
0.8158	Intermediate Similarity	NPC192046
0.8158	Intermediate Similarity	NPC302578
0.8158	Intermediate Similarity	NPC128951
0.8158	Intermediate Similarity	NPC171658
0.8158	Intermediate Similarity	NPC475031
0.8158	Intermediate Similarity	NPC476233
0.8158	Intermediate Similarity	NPC477227
0.8158	Intermediate Similarity	NPC105208
0.8143	Intermediate Similarity	NPC472946
0.8133	Intermediate Similarity	NPC200243
0.8133	Intermediate Similarity	NPC273366
0.8133	Intermediate Similarity	NPC230704
0.8133	Intermediate Similarity	NPC70982
0.8101	Intermediate Similarity	NPC477286
0.8101	Intermediate Similarity	NPC286719
0.8082	Intermediate Similarity	NPC63588
0.8082	Intermediate Similarity	NPC251201
0.8082	Intermediate Similarity	NPC232925
0.806	Intermediate Similarity	NPC476735
0.8056	Intermediate Similarity	NPC475893
0.8052	Intermediate Similarity	NPC67657
0.8052	Intermediate Similarity	NPC472342
0.8052	Intermediate Similarity	NPC18857
0.8049	Intermediate Similarity	NPC202937
0.8026	Intermediate Similarity	NPC473916
0.8026	Intermediate Similarity	NPC477602
0.8026	Intermediate Similarity	NPC477601
0.8	Intermediate Similarity	NPC49168
0.8	Intermediate Similarity	NPC470070
0.8	Intermediate Similarity	NPC272359
0.8	Intermediate Similarity	NPC196358
0.8	Intermediate Similarity	NPC304499
0.8	Intermediate Similarity	NPC5046
0.8	Intermediate Similarity	NPC254509
0.8	Intermediate Similarity	NPC145552
0.7973	Intermediate Similarity	NPC478103
0.7949	Intermediate Similarity	NPC269333
0.7949	Intermediate Similarity	NPC220379
0.7945	Intermediate Similarity	NPC470833
0.7927	Intermediate Similarity	NPC155531
0.7927	Intermediate Similarity	NPC215968
0.7922	Intermediate Similarity	NPC331618
0.7922	Intermediate Similarity	NPC257191
0.7922	Intermediate Similarity	NPC212453
0.7922	Intermediate Similarity	NPC264602
0.7917	Intermediate Similarity	NPC204233
0.791	Intermediate Similarity	NPC135438
0.7895	Intermediate Similarity	NPC472952
0.7895	Intermediate Similarity	NPC472950
0.7895	Intermediate Similarity	NPC186851
0.7895	Intermediate Similarity	NPC3403
0.7887	Intermediate Similarity	NPC80463
0.7882	Intermediate Similarity	NPC473066
0.7875	Intermediate Similarity	NPC60018
0.7875	Intermediate Similarity	NPC202688
0.7875	Intermediate Similarity	NPC154043
0.7867	Intermediate Similarity	NPC232112
0.7867	Intermediate Similarity	NPC195489
0.7857	Intermediate Similarity	NPC228059
0.7848	Intermediate Similarity	NPC13554
0.7831	Intermediate Similarity	NPC43912
0.7831	Intermediate Similarity	NPC140446
0.7821	Intermediate Similarity	NPC102708
0.7808	Intermediate Similarity	NPC474756
0.7805	Intermediate Similarity	NPC290612
0.7778	Intermediate Similarity	NPC472744
0.7763	Intermediate Similarity	NPC472945
0.7763	Intermediate Similarity	NPC472944
0.775	Intermediate Similarity	NPC73515
0.775	Intermediate Similarity	NPC77311
0.7733	Intermediate Similarity	NPC320549
0.7733	Intermediate Similarity	NPC151018
0.7733	Intermediate Similarity	NPC156277
0.7733	Intermediate Similarity	NPC111234
0.7733	Intermediate Similarity	NPC58057
0.7711	Intermediate Similarity	NPC103782
0.7711	Intermediate Similarity	NPC125399
0.7711	Intermediate Similarity	NPC80700
0.7711	Intermediate Similarity	NPC477283
0.7711	Intermediate Similarity	NPC114378
0.7701	Intermediate Similarity	NPC175
0.7701	Intermediate Similarity	NPC191915
0.7701	Intermediate Similarity	NPC151214
0.7692	Intermediate Similarity	NPC23884
0.7683	Intermediate Similarity	NPC474996
0.7683	Intermediate Similarity	NPC320824
0.7662	Intermediate Similarity	NPC174964
0.7662	Intermediate Similarity	NPC178383
0.7662	Intermediate Similarity	NPC212733
0.7662	Intermediate Similarity	NPC195155
0.7662	Intermediate Similarity	NPC185536
0.7662	Intermediate Similarity	NPC231256
0.7662	Intermediate Similarity	NPC212879
0.7662	Intermediate Similarity	NPC240235
0.7662	Intermediate Similarity	NPC104387
0.7662	Intermediate Similarity	NPC97534
0.7654	Intermediate Similarity	NPC470611
0.7647	Intermediate Similarity	NPC131466
0.7647	Intermediate Similarity	NPC82955
0.7647	Intermediate Similarity	NPC236588
0.7632	Intermediate Similarity	NPC253805
0.7619	Intermediate Similarity	NPC210658
0.7619	Intermediate Similarity	NPC161928
0.7614	Intermediate Similarity	NPC473067
0.7614	Intermediate Similarity	NPC473065
0.7614	Intermediate Similarity	NPC473064
0.7606	Intermediate Similarity	NPC249078
0.7606	Intermediate Similarity	NPC290791
0.7606	Intermediate Similarity	NPC292419
0.7606	Intermediate Similarity	NPC236099
0.7606	Intermediate Similarity	NPC209686
0.76	Intermediate Similarity	NPC45296
0.7595	Intermediate Similarity	NPC65897

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 NPC473238 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	4427
0.2-0.3	3082
0.3-0.4	723
0.4-0.5	211
0.5-0.6	230
0.6-0.7	42
0.7-0.8	21
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8986	High Similarity	NPD4267	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD4787	Phase 1
0.7733	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6117	Approved
0.7532	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6116	Phase 1
0.7467	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7525	Registered
0.7375	Intermediate Similarity	NPD6114	Approved
0.7375	Intermediate Similarity	NPD6697	Approved
0.7375	Intermediate Similarity	NPD6118	Approved
0.7375	Intermediate Similarity	NPD6115	Approved
0.7333	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5360	Phase 3
0.7215	Intermediate Similarity	NPD3703	Phase 2
0.7195	Intermediate Similarity	NPD6928	Phase 2
0.7143	Intermediate Similarity	NPD4789	Approved
0.7143	Intermediate Similarity	NPD4244	Approved
0.7143	Intermediate Similarity	NPD4245	Approved
0.7013	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD8171	Discontinued
0.6933	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4758	Discontinued
0.68	Remote Similarity	NPD371	Approved
0.679	Remote Similarity	NPD6942	Approved
0.679	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3671	Phase 1
0.6707	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD6705	Phase 1
0.6667	Remote Similarity	NPD7645	Phase 2
0.6588	Remote Similarity	NPD4748	Discontinued
0.6585	Remote Similarity	NPD3702	Approved
0.6548	Remote Similarity	NPD5364	Discontinued
0.6522	Remote Similarity	NPD8034	Phase 2
0.6522	Remote Similarity	NPD8035	Phase 2
0.6506	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6924	Approved
0.6463	Remote Similarity	NPD6926	Approved
0.642	Remote Similarity	NPD5777	Approved
0.642	Remote Similarity	NPD6081	Approved
0.6418	Remote Similarity	NPD385	Approved
0.6418	Remote Similarity	NPD384	Approved
0.6413	Remote Similarity	NPD6700	Approved
0.6413	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4224	Phase 2
0.6364	Remote Similarity	NPD4788	Approved
0.6344	Remote Similarity	NPD6703	Approved
0.6344	Remote Similarity	NPD6702	Approved
0.6333	Remote Similarity	NPD8308	Discontinued
0.6327	Remote Similarity	NPD4159	Approved
0.6304	Remote Similarity	NPD5328	Approved
0.63	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4786	Approved
0.6264	Remote Similarity	NPD7524	Approved
0.622	Remote Similarity	NPD4243	Approved
0.6186	Remote Similarity	NPD7920	Phase 3
0.6186	Remote Similarity	NPD7919	Phase 3
0.617	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD3618	Phase 1
0.6146	Remote Similarity	NPD7991	Discontinued
0.6122	Remote Similarity	NPD8088	Phase 1
0.6105	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4785	Approved
0.6071	Remote Similarity	NPD1811	Approved
0.6071	Remote Similarity	NPD1810	Approved
0.6071	Remote Similarity	NPD4784	Approved
0.6067	Remote Similarity	NPD3667	Approved
0.6061	Remote Similarity	NPD8418	Phase 2
0.6024	Remote Similarity	NPD7152	Approved
0.6024	Remote Similarity	NPD7150	Approved
0.6024	Remote Similarity	NPD7151	Approved
0.6023	Remote Similarity	NPD6931	Approved
0.6023	Remote Similarity	NPD6930	Phase 2
0.6023	Remote Similarity	NPD7509	Discontinued
0.6	Remote Similarity	NPD6695	Phase 3
0.5976	Remote Similarity	NPD6923	Approved
0.5976	Remote Similarity	NPD6922	Approved
0.596	Remote Similarity	NPD7638	Approved
0.5934	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7750	Discontinued
0.5909	Remote Similarity	NPD6929	Approved
0.5904	Remote Similarity	NPD7144	Approved
0.5904	Remote Similarity	NPD7143	Approved
0.59	Remote Similarity	NPD7640	Approved
0.59	Remote Similarity	NPD7639	Approved
0.5888	Remote Similarity	NPD8297	Approved
0.5862	Remote Similarity	NPD6932	Approved
0.5859	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD8133	Approved
0.5818	Remote Similarity	NPD7115	Discovery
0.5814	Remote Similarity	NPD5275	Approved
0.5814	Remote Similarity	NPD4190	Phase 3
0.5804	Remote Similarity	NPD8294	Approved
0.5804	Remote Similarity	NPD8377	Approved
0.5797	Remote Similarity	NPD388	Approved
0.5797	Remote Similarity	NPD386	Approved
0.5784	Remote Similarity	NPD7632	Discontinued
0.5778	Remote Similarity	NPD6902	Approved
0.5773	Remote Similarity	NPD6399	Phase 3
0.5769	Remote Similarity	NPD5739	Approved
0.5769	Remote Similarity	NPD7128	Approved
0.5769	Remote Similarity	NPD6402	Approved
0.5769	Remote Similarity	NPD6920	Discontinued
0.5769	Remote Similarity	NPD6675	Approved
0.5766	Remote Similarity	NPD7328	Approved
0.5766	Remote Similarity	NPD7327	Approved
0.5761	Remote Similarity	NPD3665	Phase 1
0.5761	Remote Similarity	NPD3666	Approved
0.5761	Remote Similarity	NPD3133	Approved
0.5758	Remote Similarity	NPD4697	Phase 3
0.5758	Remote Similarity	NPD5222	Approved
0.5758	Remote Similarity	NPD5221	Approved
0.5758	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD8378	Approved
0.5752	Remote Similarity	NPD8296	Approved
0.5752	Remote Similarity	NPD8379	Approved
0.5752	Remote Similarity	NPD8033	Approved
0.5752	Remote Similarity	NPD8335	Approved
0.5752	Remote Similarity	NPD8380	Approved
0.5743	Remote Similarity	NPD5286	Approved
0.5743	Remote Similarity	NPD4696	Approved
0.5743	Remote Similarity	NPD5285	Approved
0.5743	Remote Similarity	NPD4700	Approved
0.573	Remote Similarity	NPD6683	Phase 2
0.573	Remote Similarity	NPD4195	Approved
0.5714	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD2686	Approved
0.5714	Remote Similarity	NPD7516	Approved
0.5714	Remote Similarity	NPD2687	Approved
0.5714	Remote Similarity	NPD2254	Approved
0.57	Remote Similarity	NPD5173	Approved
0.5699	Remote Similarity	NPD6893	Approved
0.5688	Remote Similarity	NPD4632	Approved
0.5686	Remote Similarity	NPD5223	Approved
0.5682	Remote Similarity	NPD5776	Phase 2
0.5682	Remote Similarity	NPD6925	Approved
0.567	Remote Similarity	NPD7515	Phase 2
0.5667	Remote Similarity	NPD7514	Phase 3
0.566	Remote Similarity	NPD6899	Approved
0.566	Remote Similarity	NPD6881	Approved
0.566	Remote Similarity	NPD7320	Approved
0.566	Remote Similarity	NPD8174	Phase 2
0.5648	Remote Similarity	NPD8130	Phase 1
0.5631	Remote Similarity	NPD5226	Approved
0.5631	Remote Similarity	NPD5224	Approved
0.5631	Remote Similarity	NPD5225	Approved
0.5631	Remote Similarity	NPD4633	Approved
0.5631	Remote Similarity	NPD5211	Phase 2
0.5625	Remote Similarity	NPD4753	Phase 2
0.5618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7145	Approved
0.5607	Remote Similarity	NPD6372	Approved
0.5607	Remote Similarity	NPD6373	Approved
0.5607	Remote Similarity	NPD4061	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