NPASS Compound

Structure

NPC252901 OpenBabel07101719512D 24 27 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -1.0000 0.0000 C 0 0 0 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 0.5000 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 0.0000 0.0000 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 1.7321 2.0000 0.0000 C 0 0 1 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 -2.5981 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 1.7321 0.0000 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 0 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 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 Cl 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 1 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 1 0 0 0 18 22 1 0 0 0 0 20 21 1 1 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	362.428
LogP:	6.43
LogD:	4.691
LogS:	-6.085
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	4.595
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.762
MDCK Permeability:	1.555208655190654e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.813

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	98.71145629882812%
Volume Distribution (VD):	3.413
Pgp-substrate:	1.5759541988372803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.222
CYP1A2-substrate:	0.62
CYP2C19-inhibitor:	0.494
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.433
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.451
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.543
CYP3A4-substrate:	0.467

ADMET: Excretion

Clearance (CL):	11.507
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.538
Drug-inuced Liver Injury (DILI):	0.29
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.498
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.768
Carcinogencity:	0.47
Eye Corrosion:	0.008
Eye Irritation:	0.52
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC252901

Natural Product ID:	NPC252901
*Common Name:**	WTHNHDFNKOVPBI-LNWOYWOMSA-N
IUPAC Name:	n.a.
Synonyms:	6'-Chloroaureol
Standard InCHIKey:	WTHNHDFNKOVPBI-LNWOYWOMSA-N
Standard InCHI:	InChI=1S/C21H29ClO2/c1-13-6-9-17-19(2,3)10-5-11-21(17)20(13,4)12-14-16(24-21)8-7-15(23)18(14)22/h7-8,13,17,23H,5-6,9-12H2,1-4H3/t13-,17-,20+,21-/m0/s1
SMILES:	C[C@H]1CC[C@@H]2[C@]3([C@]1(C)Cc1c(O3)ccc(c1Cl)O)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457256
PubChem CID:	10450460
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO20958	Smenospongia aurea	Species	Thorectidae	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	2

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.4	ug.mL-1	PMID[506740]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	38.0	%	PMID[506740]
NPT2	Others	Unspecified		Selectivity Index	>	1.4	n.a.	PMID[506740]

☑ 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 NPC252901 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	570
0.1-0.2	2099
0.2-0.3	5797
0.3-0.4	12580
0.4-0.5	6059
0.5-0.6	12359
0.6-0.7	3072
0.7-0.8	149
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8722	High Similarity	NPC248557
0.8467	Intermediate Similarity	NPC47288
0.8286	Intermediate Similarity	NPC153019
0.8222	Intermediate Similarity	NPC475839
0.8169	Intermediate Similarity	NPC211352
0.8134	Intermediate Similarity	NPC51341
0.8099	Intermediate Similarity	NPC289624
0.8099	Intermediate Similarity	NPC27578
0.8071	Intermediate Similarity	NPC176590
0.8043	Intermediate Similarity	NPC61685
0.8	Intermediate Similarity	NPC474610
0.8	Intermediate Similarity	NPC471449
0.7956	Intermediate Similarity	NPC168707
0.7956	Intermediate Similarity	NPC48623
0.7929	Intermediate Similarity	NPC128321
0.7902	Intermediate Similarity	NPC193334
0.7883	Intermediate Similarity	NPC45663
0.7852	Intermediate Similarity	NPC238176
0.7852	Intermediate Similarity	NPC187993
0.7838	Intermediate Similarity	NPC472794
0.7838	Intermediate Similarity	NPC79372
0.7838	Intermediate Similarity	NPC76312
0.7838	Intermediate Similarity	NPC473049
0.7785	Intermediate Similarity	NPC472792
0.7785	Intermediate Similarity	NPC472791
0.7778	Intermediate Similarity	NPC69539
0.7762	Intermediate Similarity	NPC222108
0.7762	Intermediate Similarity	NPC96719
0.7733	Intermediate Similarity	NPC323126
0.7704	Intermediate Similarity	NPC473718
0.7681	Intermediate Similarity	NPC474131
0.7669	Intermediate Similarity	NPC77772
0.7664	Intermediate Similarity	NPC139047
0.7655	Intermediate Similarity	NPC474200
0.7651	Intermediate Similarity	NPC265335
0.7647	Intermediate Similarity	NPC242580
0.7647	Intermediate Similarity	NPC126759
0.7647	Intermediate Similarity	NPC236070
0.7632	Intermediate Similarity	NPC474599
0.763	Intermediate Similarity	NPC471534
0.7612	Intermediate Similarity	NPC474920
0.7609	Intermediate Similarity	NPC32152
0.7606	Intermediate Similarity	NPC28476
0.7606	Intermediate Similarity	NPC133407
0.7554	Intermediate Similarity	NPC232295
0.7552	Intermediate Similarity	NPC8058
0.7537	Intermediate Similarity	NPC470770
0.7537	Intermediate Similarity	NPC275627
0.7537	Intermediate Similarity	NPC266937
0.7535	Intermediate Similarity	NPC33402
0.7518	Intermediate Similarity	NPC141001
0.7518	Intermediate Similarity	NPC473464
0.7518	Intermediate Similarity	NPC476332
0.7517	Intermediate Similarity	NPC206028
0.75	Intermediate Similarity	NPC212559
0.75	Intermediate Similarity	NPC71372
0.75	Intermediate Similarity	NPC473134
0.75	Intermediate Similarity	NPC129176
0.7484	Intermediate Similarity	NPC56379
0.7483	Intermediate Similarity	NPC85595
0.7481	Intermediate Similarity	NPC177962
0.7481	Intermediate Similarity	NPC98372
0.7481	Intermediate Similarity	NPC62867
0.7468	Intermediate Similarity	NPC472457
0.7468	Intermediate Similarity	NPC90645
0.7466	Intermediate Similarity	NPC196193
0.7465	Intermediate Similarity	NPC261992
0.745	Intermediate Similarity	NPC327382
0.7447	Intermediate Similarity	NPC14287
0.7429	Intermediate Similarity	NPC260832
0.7429	Intermediate Similarity	NPC135467
0.7429	Intermediate Similarity	NPC67791
0.7415	Intermediate Similarity	NPC258073
0.7413	Intermediate Similarity	NPC474237
0.741	Intermediate Similarity	NPC283616
0.7397	Intermediate Similarity	NPC246991
0.7397	Intermediate Similarity	NPC472797
0.7397	Intermediate Similarity	NPC16577
0.7394	Intermediate Similarity	NPC188997
0.7394	Intermediate Similarity	NPC46586
0.7394	Intermediate Similarity	NPC204535
0.7379	Intermediate Similarity	NPC186889
0.7379	Intermediate Similarity	NPC26576
0.7368	Intermediate Similarity	NPC320439
0.7365	Intermediate Similarity	NPC472798
0.7361	Intermediate Similarity	NPC252962
0.7343	Intermediate Similarity	NPC474130
0.7343	Intermediate Similarity	NPC96940
0.7325	Intermediate Similarity	NPC212142
0.732	Intermediate Similarity	NPC474850
0.732	Intermediate Similarity	NPC474851
0.7313	Intermediate Similarity	NPC146096
0.7297	Intermediate Similarity	NPC160623
0.7297	Intermediate Similarity	NPC472590
0.7292	Intermediate Similarity	NPC190086
0.7292	Intermediate Similarity	NPC147896
0.7292	Intermediate Similarity	NPC276962
0.729	Intermediate Similarity	NPC316691
0.7279	Intermediate Similarity	NPC472796
0.7279	Intermediate Similarity	NPC266868
0.7279	Intermediate Similarity	NPC472795
0.7273	Intermediate Similarity	NPC152946
0.7273	Intermediate Similarity	NPC186033
0.7273	Intermediate Similarity	NPC302211
0.7254	Intermediate Similarity	NPC473875
0.7254	Intermediate Similarity	NPC100108
0.7254	Intermediate Similarity	NPC277798
0.7248	Intermediate Similarity	NPC139335
0.7248	Intermediate Similarity	NPC469611
0.7244	Intermediate Similarity	NPC471600
0.7241	Intermediate Similarity	NPC4286
0.7241	Intermediate Similarity	NPC76119
0.7239	Intermediate Similarity	NPC233320
0.7233	Intermediate Similarity	NPC158784
0.7233	Intermediate Similarity	NPC195561
0.723	Intermediate Similarity	NPC472793
0.723	Intermediate Similarity	NPC249425
0.723	Intermediate Similarity	NPC196621
0.723	Intermediate Similarity	NPC475880
0.723	Intermediate Similarity	NPC473048
0.7211	Intermediate Similarity	NPC211179
0.7211	Intermediate Similarity	NPC81261
0.7211	Intermediate Similarity	NPC223912
0.7211	Intermediate Similarity	NPC38604
0.7206	Intermediate Similarity	NPC141782
0.72	Intermediate Similarity	NPC469610
0.7197	Intermediate Similarity	NPC471608
0.7194	Intermediate Similarity	NPC283169
0.719	Intermediate Similarity	NPC19869
0.7188	Intermediate Similarity	NPC302915
0.7188	Intermediate Similarity	NPC2745
0.7183	Intermediate Similarity	NPC103916
0.7181	Intermediate Similarity	NPC244888
0.7181	Intermediate Similarity	NPC8899
0.7181	Intermediate Similarity	NPC164804
0.7181	Intermediate Similarity	NPC211413
0.7181	Intermediate Similarity	NPC473047
0.7181	Intermediate Similarity	NPC118683
0.7181	Intermediate Similarity	NPC293203
0.7181	Intermediate Similarity	NPC68205
0.7171	Intermediate Similarity	NPC472800
0.7164	Intermediate Similarity	NPC53740
0.7162	Intermediate Similarity	NPC210655
0.7162	Intermediate Similarity	NPC185313
0.7152	Intermediate Similarity	NPC473107
0.7152	Intermediate Similarity	NPC27394
0.7143	Intermediate Similarity	NPC46978
0.7143	Intermediate Similarity	NPC290470
0.7143	Intermediate Similarity	NPC157783
0.7143	Intermediate Similarity	NPC471668
0.7143	Intermediate Similarity	NPC154256
0.7143	Intermediate Similarity	NPC308828
0.7143	Intermediate Similarity	NPC221134
0.7143	Intermediate Similarity	NPC156298
0.7143	Intermediate Similarity	NPC325860
0.7143	Intermediate Similarity	NPC312105
0.7134	Intermediate Similarity	NPC292256
0.7133	Intermediate Similarity	NPC189482
0.7133	Intermediate Similarity	NPC218753
0.7133	Intermediate Similarity	NPC96423
0.7123	Intermediate Similarity	NPC124030
0.7122	Intermediate Similarity	NPC268160
0.7114	Intermediate Similarity	NPC475102
0.7114	Intermediate Similarity	NPC325003
0.7113	Intermediate Similarity	NPC323074
0.7097	Intermediate Similarity	NPC131379
0.7095	Intermediate Similarity	NPC201069
0.7095	Intermediate Similarity	NPC53986
0.7095	Intermediate Similarity	NPC38664
0.709	Intermediate Similarity	NPC47284
0.7089	Intermediate Similarity	NPC475896
0.7086	Intermediate Similarity	NPC77196
0.7086	Intermediate Similarity	NPC138940
0.7083	Intermediate Similarity	NPC476165
0.7075	Intermediate Similarity	NPC26879
0.7075	Intermediate Similarity	NPC230479
0.7075	Intermediate Similarity	NPC283049
0.7075	Intermediate Similarity	NPC170485
0.7075	Intermediate Similarity	NPC50315
0.7071	Intermediate Similarity	NPC469719
0.7071	Intermediate Similarity	NPC301321
0.7071	Intermediate Similarity	NPC147179
0.7067	Intermediate Similarity	NPC474143
0.7067	Intermediate Similarity	NPC474246
0.7063	Intermediate Similarity	NPC325544
0.7063	Intermediate Similarity	NPC318581
0.7063	Intermediate Similarity	NPC477037
0.7059	Intermediate Similarity	NPC194847
0.7059	Intermediate Similarity	NPC126101
0.7059	Intermediate Similarity	NPC21797
0.7059	Intermediate Similarity	NPC173660
0.705	Intermediate Similarity	NPC141003
0.705	Intermediate Similarity	NPC35344
0.7047	Intermediate Similarity	NPC93962
0.7047	Intermediate Similarity	NPC271832
0.7047	Intermediate Similarity	NPC59654
0.7042	Intermediate Similarity	NPC63010
0.7042	Intermediate Similarity	NPC469609
0.7039	Intermediate Similarity	NPC115335
0.7039	Intermediate Similarity	NPC141023

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 NPC252901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	461
0.1-0.2	1011
0.2-0.3	1663
0.3-0.4	2988
0.4-0.5	1790
0.5-0.6	1014
0.6-0.7	210
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7836	Intermediate Similarity	NPD6671	Approved
0.766	Intermediate Similarity	NPD6696	Suspended
0.7647	Intermediate Similarity	NPD7340	Approved
0.7613	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1398	Phase 1
0.7397	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD2861	Phase 2
0.7355	Intermediate Similarity	NPD7041	Phase 2
0.7355	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4749	Approved
0.7219	Intermediate Similarity	NPD4538	Approved
0.7219	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4536	Approved
0.7124	Intermediate Similarity	NPD6099	Approved
0.7124	Intermediate Similarity	NPD6100	Approved
0.7114	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5327	Phase 3
0.7095	Intermediate Similarity	NPD4908	Phase 1
0.7075	Intermediate Similarity	NPD4624	Approved
0.7063	Intermediate Similarity	NPD4589	Approved
0.7059	Intermediate Similarity	NPD5960	Phase 3
0.7059	Intermediate Similarity	NPD5588	Approved
0.7048	Intermediate Similarity	NPD3365	Discontinued
0.7039	Intermediate Similarity	NPD6353	Approved
0.702	Intermediate Similarity	NPD4140	Approved
0.6986	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7635	Approved
0.6974	Remote Similarity	NPD5735	Approved
0.6972	Remote Similarity	NPD7644	Approved
0.6966	Remote Similarity	NPD1611	Approved
0.6962	Remote Similarity	NPD5058	Phase 3
0.6943	Remote Similarity	NPD4535	Phase 3
0.6936	Remote Similarity	NPD3303	Discontinued
0.6928	Remote Similarity	NPD4097	Suspended
0.6918	Remote Similarity	NPD2233	Approved
0.6918	Remote Similarity	NPD2230	Approved
0.6918	Remote Similarity	NPD2232	Approved
0.6917	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD968	Approved
0.6908	Remote Similarity	NPD4060	Phase 1
0.6897	Remote Similarity	NPD3496	Discontinued
0.6884	Remote Similarity	NPD5451	Approved
0.6875	Remote Similarity	NPD1578	Phase 2
0.6863	Remote Similarity	NPD1184	Approved
0.6855	Remote Similarity	NPD6815	Approved
0.6849	Remote Similarity	NPD1610	Phase 2
0.6846	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6516	Phase 2
0.6828	Remote Similarity	NPD5846	Approved
0.6821	Remote Similarity	NPD7095	Approved
0.6797	Remote Similarity	NPD3620	Phase 2
0.6797	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4359	Approved
0.6733	Remote Similarity	NPD6584	Phase 3
0.6732	Remote Similarity	NPD8032	Phase 2
0.6712	Remote Similarity	NPD4059	Approved
0.6712	Remote Similarity	NPD4626	Approved
0.6709	Remote Similarity	NPD7037	Approved
0.6709	Remote Similarity	NPD4534	Discontinued
0.6691	Remote Similarity	NPD9500	Approved
0.669	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5929	Approved
0.6645	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5585	Approved
0.6626	Remote Similarity	NPD6090	Discontinued
0.6619	Remote Similarity	NPD2342	Discontinued
0.6599	Remote Similarity	NPD1778	Approved
0.6599	Remote Similarity	NPD3019	Approved
0.6597	Remote Similarity	NPD7157	Approved
0.6579	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD454	Approved
0.6577	Remote Similarity	NPD2235	Phase 2
0.6577	Remote Similarity	NPD2231	Phase 2
0.6567	Remote Similarity	NPD288	Approved
0.6562	Remote Similarity	NPD6674	Discontinued
0.6561	Remote Similarity	NPD7097	Phase 1
0.6558	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7985	Registered
0.6556	Remote Similarity	NPD987	Approved
0.6541	Remote Similarity	NPD5763	Approved
0.6541	Remote Similarity	NPD7030	Discontinued
0.6541	Remote Similarity	NPD5762	Approved
0.6541	Remote Similarity	NPD2346	Discontinued
0.6533	Remote Similarity	NPD6582	Phase 2
0.6533	Remote Similarity	NPD6583	Phase 3
0.6531	Remote Similarity	NPD5691	Approved
0.6528	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6273	Approved
0.6522	Remote Similarity	NPD7003	Approved
0.651	Remote Similarity	NPD3092	Approved
0.6506	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5535	Approved
0.65	Remote Similarity	NPD5958	Discontinued
0.65	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD844	Approved
0.649	Remote Similarity	NPD8651	Approved
0.6486	Remote Similarity	NPD2932	Approved
0.6483	Remote Similarity	NPD709	Approved
0.648	Remote Similarity	NPD3337	Discontinued
0.6474	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3109	Approved
0.6474	Remote Similarity	NPD3110	Approved
0.6474	Remote Similarity	NPD2238	Phase 2
0.6474	Remote Similarity	NPD1613	Approved
0.6471	Remote Similarity	NPD5736	Approved
0.6471	Remote Similarity	NPD3020	Approved
0.6471	Remote Similarity	NPD1712	Approved
0.6471	Remote Similarity	NPD2237	Approved
0.6467	Remote Similarity	NPD1608	Approved
0.6467	Remote Similarity	NPD1157	Approved
0.6463	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1548	Phase 1
0.6458	Remote Similarity	NPD5283	Phase 1
0.6457	Remote Similarity	NPD5880	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD2684	Approved
0.6452	Remote Similarity	NPD3268	Approved
0.6452	Remote Similarity	NPD7294	Phase 1
0.6447	Remote Similarity	NPD3094	Phase 2
0.6447	Remote Similarity	NPD4098	Discontinued
0.6443	Remote Similarity	NPD915	Approved
0.6438	Remote Similarity	NPD2376	Approved
0.6438	Remote Similarity	NPD2378	Approved
0.6438	Remote Similarity	NPD2377	Approved
0.6424	Remote Similarity	NPD6542	Approved
0.6424	Remote Similarity	NPD6543	Approved
0.6424	Remote Similarity	NPD6539	Approved
0.6424	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6540	Phase 3
0.6423	Remote Similarity	NPD1616	Discontinued
0.6419	Remote Similarity	NPD3444	Approved
0.6419	Remote Similarity	NPD3445	Approved
0.6419	Remote Similarity	NPD3443	Approved
0.6408	Remote Similarity	NPD4750	Phase 3
0.6392	Remote Similarity	NPD2157	Approved
0.6387	Remote Similarity	NPD1024	Discontinued
0.6386	Remote Similarity	NPD5699	Approved
0.6383	Remote Similarity	NPD290	Approved
0.6382	Remote Similarity	NPD6538	Approved
0.6382	Remote Similarity	NPD6541	Approved
0.6382	Remote Similarity	NPD1283	Approved
0.6376	Remote Similarity	NPD2668	Approved
0.6376	Remote Similarity	NPD3095	Discontinued
0.6376	Remote Similarity	NPD2667	Approved
0.6375	Remote Similarity	NPD2935	Discontinued
0.6364	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD1972	Approved
0.6347	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD1973	Approved
0.6343	Remote Similarity	NPD845	Approved
0.6337	Remote Similarity	NPD7833	Phase 2
0.6337	Remote Similarity	NPD4064	Discontinued
0.6337	Remote Similarity	NPD7831	Phase 2
0.6337	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3364	Phase 3
0.6323	Remote Similarity	NPD2605	Approved
0.6323	Remote Similarity	NPD2606	Approved
0.6319	Remote Similarity	NPD228	Approved
0.6312	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5894	Phase 2
0.631	Remote Similarity	NPD3226	Approved
0.6309	Remote Similarity	NPD1651	Approved
0.6307	Remote Similarity	NPD2489	Approved
0.6307	Remote Similarity	NPD27	Approved
0.6306	Remote Similarity	NPD7477	Discontinued
0.6306	Remote Similarity	NPD6663	Approved
0.6296	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3021	Approved
0.6294	Remote Similarity	NPD5722	Discontinued
0.6294	Remote Similarity	NPD3022	Approved
0.6291	Remote Similarity	NPD1535	Discovery
0.6289	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3051	Approved
0.6282	Remote Similarity	NPD5156	Approved
0.6282	Remote Similarity	NPD5155	Approved
0.6276	Remote Similarity	NPD7843	Approved
0.6273	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD17	Approved
0.6259	Remote Similarity	NPD2557	Approved
0.6259	Remote Similarity	NPD6387	Discontinued
0.6258	Remote Similarity	NPD1416	Approved
0.625	Remote Similarity	NPD1481	Phase 2
0.625	Remote Similarity	NPD1809	Phase 2
0.625	Remote Similarity	NPD2969	Approved
0.625	Remote Similarity	NPD2859	Approved
0.625	Remote Similarity	NPD2970	Approved
0.625	Remote Similarity	NPD2860	Approved
0.6242	Remote Similarity	NPD6798	Discontinued
0.6229	Remote Similarity	NPD6959	Discontinued
0.6229	Remote Similarity	NPD8127	Discontinued
0.6226	Remote Similarity	NPD5124	Phase 1
0.6226	Remote Similarity	NPD3657	Discovery
0.6226	Remote Similarity	NPD6355	Discontinued

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