NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	362.06
Volume:	335.156
LogP:	3.067
LogD:	2.403
LogS:	-3.938
# Rotatable Bonds:	3
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	3.966
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.095
MDCK Permeability:	7.880140401539393e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.183

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	96.49445343017578%
Volume Distribution (VD):	0.893
Pgp-substrate:	3.8254189491271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.724
CYP2C19-inhibitor:	0.261
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.628
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.732
CYP3A4-inhibitor:	0.454
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	7.917
Half-life (T1/2):	0.617

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.632
Drug-inuced Liver Injury (DILI):	0.684
AMES Toxicity:	0.756
Rat Oral Acute Toxicity:	0.672
Maximum Recommended Daily Dose:	0.12
Skin Sensitization:	0.691
Carcinogencity:	0.911
Eye Corrosion:	0.004
Eye Irritation:	0.545
Respiratory Toxicity:	0.142

Download Data

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

Natural Product: NPC477834

Natural Product ID:	NPC477834
*Common Name:**	2-[1-(Chloromethyl)-1,2-dihydroxyethyl]-10-hydroxy-1,2-dihydro-11H-furo[3,2-a]xanthene-11-one
IUPAC Name:	2-(1-chloro-2,3-dihydroxypropan-2-yl)-10-hydroxy-1,2-dihydrofuro[3,2-a]xanthen-11-one
Synonyms:	psoroxanthin chlorohydrin
Standard InCHIKey:	RJDOXCXLBLHXNV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15ClO6/c19-7-18(23,8-20)14-6-9-11(25-14)4-5-13-15(9)17(22)16-10(21)2-1-3-12(16)24-13/h1-5,14,20-21,23H,6-8H2
SMILES:	C1C(OC2=C1C3=C(C=C2)OC4=CC=CC(=C4C3=O)O)C(CO)(CCl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24854051
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO33564	Psorospermum cf. molluscum	Species	Hypericaceae	Eukaryota	n.a.	Madagascar rain forest	n.a.	PMID[18247570]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	42	nM	PMID[18247570]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	68	nM	PMID[18247570]
NPT5611	Cell Line	ABAE	Homo sapiens	IC50	=	4	nM	PMID[18247570]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	2000	nM	PMID[18247570]

☑ 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 NPC477834 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	451
0.1-0.2	1812
0.2-0.3	4409
0.3-0.4	10979
0.4-0.5	7570
0.5-0.6	4262
0.6-0.7	6062
0.7-0.8	5423
0.8-0.85	1644
0.85-0.9	82
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9363	High Similarity	NPC477833
0.8916	High Similarity	NPC474004
0.8896	High Similarity	NPC472402
0.8868	High Similarity	NPC474843
0.8841	High Similarity	NPC475985
0.8735	High Similarity	NPC170245
0.872	High Similarity	NPC96031
0.8712	High Similarity	NPC329091
0.8675	High Similarity	NPC326520
0.8659	High Similarity	NPC470810
0.8659	High Similarity	NPC471976
0.8642	High Similarity	NPC175192
0.8616	High Similarity	NPC218569
0.8606	High Similarity	NPC3629
0.8598	High Similarity	NPC476242
0.8589	High Similarity	NPC235165
0.8589	High Similarity	NPC201837
0.8589	High Similarity	NPC255106
0.8589	High Similarity	NPC24640
0.8589	High Similarity	NPC164427
0.8571	High Similarity	NPC117854
0.8571	High Similarity	NPC472636
0.8571	High Similarity	NPC207346
0.8571	High Similarity	NPC204515
0.8571	High Similarity	NPC46564
0.8571	High Similarity	NPC6588
0.8571	High Similarity	NPC225419
0.8571	High Similarity	NPC477154
0.8563	High Similarity	NPC473286
0.8562	High Similarity	NPC277032
0.8554	High Similarity	NPC472964
0.8554	High Similarity	NPC473961
0.8553	High Similarity	NPC21835
0.8545	High Similarity	NPC263449
0.8545	High Similarity	NPC472902
0.8545	High Similarity	NPC139036
0.8537	High Similarity	NPC210084
0.8537	High Similarity	NPC162869
0.8537	High Similarity	NPC474208
0.8537	High Similarity	NPC300727
0.8537	High Similarity	NPC48208
0.8537	High Similarity	NPC196448
0.8537	High Similarity	NPC475267
0.8537	High Similarity	NPC474836
0.8537	High Similarity	NPC241904
0.8537	High Similarity	NPC99597
0.8537	High Similarity	NPC156057
0.8528	High Similarity	NPC67396
0.8528	High Similarity	NPC37392
0.8519	High Similarity	NPC321363
0.8519	High Similarity	NPC473996
0.8519	High Similarity	NPC253904
0.8519	High Similarity	NPC281272
0.8509	High Similarity	NPC227122
0.8509	High Similarity	NPC267117
0.8503	High Similarity	NPC7483
0.8503	High Similarity	NPC470178
0.8503	High Similarity	NPC124038
0.85	High Similarity	NPC191634
0.8494	Intermediate Similarity	NPC308992
0.8494	Intermediate Similarity	NPC30655
0.8494	Intermediate Similarity	NPC61010
0.8494	Intermediate Similarity	NPC474186
0.8494	Intermediate Similarity	NPC474187
0.8494	Intermediate Similarity	NPC74854
0.8494	Intermediate Similarity	NPC45124
0.8485	Intermediate Similarity	NPC152904
0.8476	Intermediate Similarity	NPC274730
0.8476	Intermediate Similarity	NPC313922
0.8466	Intermediate Similarity	NPC203080
0.8466	Intermediate Similarity	NPC89474
0.8466	Intermediate Similarity	NPC280530
0.8466	Intermediate Similarity	NPC178964
0.8466	Intermediate Similarity	NPC95842
0.8466	Intermediate Similarity	NPC135522
0.8462	Intermediate Similarity	NPC42892
0.8457	Intermediate Similarity	NPC472422
0.8457	Intermediate Similarity	NPC474772
0.8457	Intermediate Similarity	NPC472580
0.8457	Intermediate Similarity	NPC471677
0.8457	Intermediate Similarity	NPC471676
0.8457	Intermediate Similarity	NPC472420
0.8457	Intermediate Similarity	NPC202157
0.8457	Intermediate Similarity	NPC471229
0.8457	Intermediate Similarity	NPC474744
0.8457	Intermediate Similarity	NPC472423
0.8457	Intermediate Similarity	NPC471675
0.8457	Intermediate Similarity	NPC117579
0.8457	Intermediate Similarity	NPC244577
0.8457	Intermediate Similarity	NPC263384
0.8452	Intermediate Similarity	NPC239752
0.8452	Intermediate Similarity	NPC472450
0.8452	Intermediate Similarity	NPC275780
0.8452	Intermediate Similarity	NPC224280
0.8452	Intermediate Similarity	NPC234052
0.8443	Intermediate Similarity	NPC229632
0.8443	Intermediate Similarity	NPC472635
0.8443	Intermediate Similarity	NPC478229
0.8438	Intermediate Similarity	NPC44721
0.8438	Intermediate Similarity	NPC176869
0.8438	Intermediate Similarity	NPC476182
0.8438	Intermediate Similarity	NPC122828
0.8438	Intermediate Similarity	NPC211466
0.8438	Intermediate Similarity	NPC71055
0.8438	Intermediate Similarity	NPC40086
0.8438	Intermediate Similarity	NPC3779
0.8434	Intermediate Similarity	NPC475886
0.8434	Intermediate Similarity	NPC228785
0.8434	Intermediate Similarity	NPC470183
0.8434	Intermediate Similarity	NPC321399
0.8434	Intermediate Similarity	NPC474287
0.8434	Intermediate Similarity	NPC472624
0.8434	Intermediate Similarity	NPC56085
0.8434	Intermediate Similarity	NPC200746
0.8434	Intermediate Similarity	NPC14353
0.8434	Intermediate Similarity	NPC36217
0.8428	Intermediate Similarity	NPC62290
0.8428	Intermediate Similarity	NPC306607
0.8428	Intermediate Similarity	NPC326506
0.8428	Intermediate Similarity	NPC49130
0.8428	Intermediate Similarity	NPC142731
0.8428	Intermediate Similarity	NPC279417
0.8428	Intermediate Similarity	NPC208176
0.8428	Intermediate Similarity	NPC4152
0.8424	Intermediate Similarity	NPC181960
0.8424	Intermediate Similarity	NPC217677
0.8424	Intermediate Similarity	NPC472910
0.8424	Intermediate Similarity	NPC472914
0.8424	Intermediate Similarity	NPC245758
0.8424	Intermediate Similarity	NPC469584
0.8424	Intermediate Similarity	NPC165977
0.8424	Intermediate Similarity	NPC472913
0.8424	Intermediate Similarity	NPC222814
0.8424	Intermediate Similarity	NPC470402
0.8424	Intermediate Similarity	NPC472911
0.8424	Intermediate Similarity	NPC96167
0.8421	Intermediate Similarity	NPC121333
0.8418	Intermediate Similarity	NPC159855
0.8418	Intermediate Similarity	NPC73028
0.8418	Intermediate Similarity	NPC310340
0.8418	Intermediate Similarity	NPC169479
0.8415	Intermediate Similarity	NPC2928
0.8415	Intermediate Similarity	NPC326910
0.8415	Intermediate Similarity	NPC472909
0.8412	Intermediate Similarity	NPC152477
0.8408	Intermediate Similarity	NPC182421
0.8408	Intermediate Similarity	NPC145673
0.8405	Intermediate Similarity	NPC199100
0.8405	Intermediate Similarity	NPC327269
0.8405	Intermediate Similarity	NPC476238
0.8405	Intermediate Similarity	NPC302950
0.8405	Intermediate Similarity	NPC260491
0.8405	Intermediate Similarity	NPC240476
0.8405	Intermediate Similarity	NPC31627
0.8405	Intermediate Similarity	NPC236637
0.8405	Intermediate Similarity	NPC9743
0.8405	Intermediate Similarity	NPC477957
0.8405	Intermediate Similarity	NPC246162
0.8405	Intermediate Similarity	NPC285623
0.8405	Intermediate Similarity	NPC120537
0.8405	Intermediate Similarity	NPC180234
0.8405	Intermediate Similarity	NPC36835
0.8405	Intermediate Similarity	NPC210597
0.8405	Intermediate Similarity	NPC61506
0.8405	Intermediate Similarity	NPC219582
0.8405	Intermediate Similarity	NPC475790
0.8402	Intermediate Similarity	NPC173292
0.8402	Intermediate Similarity	NPC128293
0.8402	Intermediate Similarity	NPC39091
0.8402	Intermediate Similarity	NPC119589
0.8402	Intermediate Similarity	NPC53640
0.8397	Intermediate Similarity	NPC18457
0.8395	Intermediate Similarity	NPC202595
0.8395	Intermediate Similarity	NPC472421
0.8395	Intermediate Similarity	NPC37348
0.8395	Intermediate Similarity	NPC62042
0.8395	Intermediate Similarity	NPC61620
0.8393	Intermediate Similarity	NPC472278
0.8393	Intermediate Similarity	NPC329669
0.8393	Intermediate Similarity	NPC236521
0.8393	Intermediate Similarity	NPC273959
0.8393	Intermediate Similarity	NPC197168
0.8393	Intermediate Similarity	NPC189473
0.8393	Intermediate Similarity	NPC220313
0.8393	Intermediate Similarity	NPC473313
0.8393	Intermediate Similarity	NPC23298
0.8393	Intermediate Similarity	NPC186686
0.8393	Intermediate Similarity	NPC152659
0.8393	Intermediate Similarity	NPC248638
0.8385	Intermediate Similarity	NPC294852
0.8385	Intermediate Similarity	NPC321011
0.8385	Intermediate Similarity	NPC35150
0.8385	Intermediate Similarity	NPC188679
0.8385	Intermediate Similarity	NPC106328
0.8385	Intermediate Similarity	NPC276930
0.8383	Intermediate Similarity	NPC173137
0.8383	Intermediate Similarity	NPC32694
0.8383	Intermediate Similarity	NPC40491
0.8383	Intermediate Similarity	NPC475883
0.8383	Intermediate Similarity	NPC278052

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 NPC477834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	927
0.2-0.3	1815
0.3-0.4	2736
0.4-0.5	1918
0.5-0.6	932
0.6-0.7	285
0.7-0.8	122
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8405	Intermediate Similarity	NPD1934	Approved
0.8242	Intermediate Similarity	NPD2801	Approved
0.8242	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4380	Phase 2
0.8165	Intermediate Similarity	NPD1549	Phase 2
0.814	Intermediate Similarity	NPD3818	Discontinued
0.8107	Intermediate Similarity	NPD5494	Approved
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD3882	Suspended
0.8025	Intermediate Similarity	NPD1511	Approved
0.8023	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3749	Approved
0.7927	Intermediate Similarity	NPD1512	Approved
0.7917	Intermediate Similarity	NPD7819	Suspended
0.791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7075	Discontinued
0.7866	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1510	Phase 2
0.7849	Intermediate Similarity	NPD6959	Discontinued
0.7841	Intermediate Similarity	NPD7074	Phase 3
0.7829	Intermediate Similarity	NPD3751	Discontinued
0.7824	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.774	Intermediate Similarity	NPD7472	Approved
0.7702	Intermediate Similarity	NPD2796	Approved
0.7701	Intermediate Similarity	NPD3787	Discontinued
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7684	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5403	Approved
0.7663	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3817	Phase 2
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD5401	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD6801	Discontinued
0.7622	Intermediate Similarity	NPD3750	Approved
0.7611	Intermediate Similarity	NPD7808	Phase 3
0.761	Intermediate Similarity	NPD1240	Approved
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD1465	Phase 2
0.76	Intermediate Similarity	NPD6232	Discontinued
0.759	Intermediate Similarity	NPD6799	Approved
0.7571	Intermediate Similarity	NPD7473	Discontinued
0.7561	Intermediate Similarity	NPD2800	Approved
0.7545	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.7516	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6100	Approved
0.7485	Intermediate Similarity	NPD6099	Approved
0.7485	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD7411	Suspended
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.7471	Intermediate Similarity	NPD3226	Approved
0.7443	Intermediate Similarity	NPD1247	Approved
0.7439	Intermediate Similarity	NPD2346	Discontinued
0.7416	Intermediate Similarity	NPD2403	Approved
0.7394	Intermediate Similarity	NPD4360	Phase 2
0.7394	Intermediate Similarity	NPD4363	Phase 3
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1613	Approved
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7351	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2344	Approved
0.7318	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3748	Approved
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7263	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3926	Phase 2
0.7263	Intermediate Similarity	NPD4361	Phase 2
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7251	Intermediate Similarity	NPD920	Approved
0.7247	Intermediate Similarity	NPD7199	Phase 2
0.7244	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7768	Phase 2
0.7212	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7207	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD5711	Approved
0.7179	Intermediate Similarity	NPD7697	Approved
0.7179	Intermediate Similarity	NPD7698	Approved
0.7179	Intermediate Similarity	NPD7696	Phase 3
0.7168	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD919	Approved
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7121	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7119	Intermediate Similarity	NPD4965	Approved
0.7119	Intermediate Similarity	NPD4967	Phase 2
0.7119	Intermediate Similarity	NPD4966	Approved
0.7118	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7783	Phase 2
0.7099	Intermediate Similarity	NPD4625	Phase 3
0.709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4287	Approved
0.7081	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2861	Phase 2
0.7072	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1470	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7874	Approved
0.705	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7228	Approved
0.7041	Intermediate Similarity	NPD1243	Approved
0.7041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD447	Suspended
0.7026	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1201	Approved
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7021	Intermediate Similarity	NPD6784	Approved
0.7021	Intermediate Similarity	NPD6785	Approved
0.7017	Intermediate Similarity	NPD7229	Phase 3
0.7015	Intermediate Similarity	NPD7801	Approved
0.701	Intermediate Similarity	NPD7700	Phase 2
0.701	Intermediate Similarity	NPD7699	Phase 2
0.7006	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD7390	Discontinued
0.6963	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2354	Approved
0.6959	Remote Similarity	NPD6190	Approved
0.6954	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5953	Discontinued
0.6933	Remote Similarity	NPD4908	Phase 1
0.6928	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD230	Phase 1
0.6923	Remote Similarity	NPD1471	Phase 3
0.6919	Remote Similarity	NPD7286	Phase 2
0.6915	Remote Similarity	NPD8151	Discontinued
0.6914	Remote Similarity	NPD1653	Approved
0.6905	Remote Similarity	NPD2799	Discontinued
0.6905	Remote Similarity	NPD5588	Approved
0.6891	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6212	Phase 3
0.6891	Remote Similarity	NPD6213	Phase 3
0.689	Remote Similarity	NPD3027	Phase 3
0.6882	Remote Similarity	NPD2424	Discontinued
0.6875	Remote Similarity	NPD1608	Approved
0.686	Remote Similarity	NPD3887	Approved
0.6848	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4749	Approved
0.6829	Remote Similarity	NPD6832	Phase 2
0.6826	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5058	Phase 3
0.6818	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7584	Approved
0.681	Remote Similarity	NPD2798	Approved
0.6809	Remote Similarity	NPD7685	Pre-registration
0.6805	Remote Similarity	NPD4308	Phase 3
0.68	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6651	Approved
0.6786	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2651	Approved
0.678	Remote Similarity	NPD2649	Approved
0.6778	Remote Similarity	NPD4288	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