NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	267.823
LogP:	2.756
LogD:	2.407
LogS:	-3.357
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	2.593
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.947
MDCK Permeability:	5.328552106220741e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.202
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	91.35149383544922%
Volume Distribution (VD):	0.773
Pgp-substrate:	8.815146446228027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.434
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.688
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	4.724
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.428
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.903
Carcinogencity:	0.035
Eye Corrosion:	0.031
Eye Irritation:	0.971
Respiratory Toxicity:	0.182

Download Data

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

Natural Product: NPC202595

Natural Product ID:	NPC202595
*Common Name:**	Leptosphaerin E
IUPAC Name:	1,3-dihydroxy-8-(hydroxymethyl)-6-methylxanthen-9-one
Synonyms:	Leptosphaerin E
Standard InCHIKey:	ZEQFLUCNLABLNA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O5/c1-7-2-8(6-16)13-11(3-7)20-12-5-9(17)4-10(18)14(12)15(13)19/h2-5,16-18H,6H2,1H3
SMILES:	Cc1cc(CO)c2c(c1)oc1cc(cc(c1c2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095459
PubChem CID:	46831409
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
NPO32944	leptosphaeria sp.	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20408555]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6578	Organism	Microdochium nivale	Microdochium nivale	IC50	>	150000.0	nM	PMID[537727]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	150000.0	nM	PMID[537727]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IC50	>	150000.0	nM	PMID[537727]

☑ 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 NPC202595 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	432
0.1-0.2	1868
0.2-0.3	4072
0.3-0.4	10186
0.4-0.5	8142
0.5-0.6	3834
0.6-0.7	5276
0.7-0.8	4762
0.8-0.85	2439
0.85-0.9	1482
0.9-0.95	187
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9653	High Similarity	NPC71055
0.9527	High Similarity	NPC135522
0.9524	High Similarity	NPC232645
0.9524	High Similarity	NPC72958
0.9517	High Similarity	NPC123202
0.9517	High Similarity	NPC22005
0.9517	High Similarity	NPC7943
0.9459	High Similarity	NPC40356
0.9459	High Similarity	NPC87708
0.9459	High Similarity	NPC154683
0.9456	High Similarity	NPC325983
0.9456	High Similarity	NPC147735
0.9452	High Similarity	NPC27221
0.9452	High Similarity	NPC7025
0.9452	High Similarity	NPC256672
0.9392	High Similarity	NPC474417
0.9392	High Similarity	NPC149526
0.9392	High Similarity	NPC478148
0.9388	High Similarity	NPC65589
0.9388	High Similarity	NPC288036
0.9388	High Similarity	NPC100985
0.9388	High Similarity	NPC97029
0.9388	High Similarity	NPC97028
0.9388	High Similarity	NPC158338
0.9375	High Similarity	NPC310340
0.9371	High Similarity	NPC275734
0.9329	High Similarity	NPC474843
0.9329	High Similarity	NPC273483
0.9324	High Similarity	NPC227122
0.9324	High Similarity	NPC255641
0.9324	High Similarity	NPC290954
0.9315	High Similarity	NPC24136
0.9315	High Similarity	NPC187282
0.9315	High Similarity	NPC290133
0.9306	High Similarity	NPC182255
0.9306	High Similarity	NPC94076
0.9276	High Similarity	NPC186113
0.9276	High Similarity	NPC85121
0.9267	High Similarity	NPC210942
0.9267	High Similarity	NPC169990
0.9262	High Similarity	NPC470569
0.9252	High Similarity	NPC289042
0.9252	High Similarity	NPC118027
0.9252	High Similarity	NPC312929
0.9252	High Similarity	NPC245584
0.9252	High Similarity	NPC126767
0.9252	High Similarity	NPC308200
0.9252	High Similarity	NPC190648
0.9252	High Similarity	NPC56433
0.9247	High Similarity	NPC470890
0.9241	High Similarity	NPC73028
0.9241	High Similarity	NPC84266
0.9236	High Similarity	NPC182421
0.9216	High Similarity	NPC470810
0.92	High Similarity	NPC217447
0.9195	High Similarity	NPC119929
0.9195	High Similarity	NPC294646
0.9195	High Similarity	NPC470107
0.9195	High Similarity	NPC470568
0.9189	High Similarity	NPC5537
0.9189	High Similarity	NPC39195
0.9189	High Similarity	NPC145467
0.9184	High Similarity	NPC472629
0.9178	High Similarity	NPC19896
0.9178	High Similarity	NPC113770
0.9161	High Similarity	NPC197168
0.9145	High Similarity	NPC146211
0.9145	High Similarity	NPC180924
0.9139	High Similarity	NPC329844
0.9139	High Similarity	NPC193200
0.9139	High Similarity	NPC178964
0.9139	High Similarity	NPC280530
0.9139	High Similarity	NPC214632
0.9139	High Similarity	NPC95842
0.9133	High Similarity	NPC258249
0.9133	High Similarity	NPC39819
0.9128	High Similarity	NPC266499
0.9128	High Similarity	NPC291049
0.9128	High Similarity	NPC471114
0.9128	High Similarity	NPC233267
0.9128	High Similarity	NPC65775
0.9128	High Similarity	NPC70764
0.9128	High Similarity	NPC10027
0.9122	High Similarity	NPC34802
0.9116	High Similarity	NPC224714
0.9116	High Similarity	NPC303185
0.9116	High Similarity	NPC184649
0.9116	High Similarity	NPC124780
0.9116	High Similarity	NPC271288
0.9116	High Similarity	NPC311144
0.9116	High Similarity	NPC469764
0.9116	High Similarity	NPC87486
0.9108	High Similarity	NPC225419
0.9103	High Similarity	NPC25361
0.9097	High Similarity	NPC473961
0.9091	High Similarity	NPC474287
0.9091	High Similarity	NPC119224
0.9091	High Similarity	NPC321399
0.9091	High Similarity	NPC475886
0.9085	High Similarity	NPC217677
0.9085	High Similarity	NPC164110
0.9085	High Similarity	NPC282390
0.9085	High Similarity	NPC272196
0.9085	High Similarity	NPC281137
0.9085	High Similarity	NPC212967
0.9085	High Similarity	NPC246647
0.9085	High Similarity	NPC201127
0.9085	High Similarity	NPC44199
0.9085	High Similarity	NPC96342
0.9085	High Similarity	NPC165977
0.9079	High Similarity	NPC175192
0.9073	High Similarity	NPC271681
0.9073	High Similarity	NPC281272
0.9073	High Similarity	NPC473967
0.9073	High Similarity	NPC175978
0.9067	High Similarity	NPC29777
0.9067	High Similarity	NPC471115
0.9067	High Similarity	NPC472633
0.9067	High Similarity	NPC37348
0.906	High Similarity	NPC37135
0.906	High Similarity	NPC105415
0.906	High Similarity	NPC186397
0.9054	High Similarity	NPC469758
0.9054	High Similarity	NPC267509
0.9054	High Similarity	NPC299011
0.9054	High Similarity	NPC196114
0.9048	High Similarity	NPC189650
0.9045	High Similarity	NPC178851
0.9041	High Similarity	NPC312391
0.9041	High Similarity	NPC96408
0.9041	High Similarity	NPC213322
0.9041	High Similarity	NPC156190
0.9041	High Similarity	NPC166689
0.9041	High Similarity	NPC17170
0.9041	High Similarity	NPC279650
0.9041	High Similarity	NPC258630
0.9041	High Similarity	NPC4743
0.9041	High Similarity	NPC324386
0.9041	High Similarity	NPC3188
0.9038	High Similarity	NPC7483
0.9038	High Similarity	NPC236132
0.9034	High Similarity	NPC316480
0.9032	High Similarity	NPC474187
0.9032	High Similarity	NPC66288
0.9032	High Similarity	NPC18380
0.9032	High Similarity	NPC475883
0.9032	High Similarity	NPC474186
0.9032	High Similarity	NPC474351
0.9026	High Similarity	NPC210459
0.9026	High Similarity	NPC329091
0.9026	High Similarity	NPC324736
0.902	High Similarity	NPC142339
0.902	High Similarity	NPC164427
0.9013	High Similarity	NPC208806
0.9013	High Similarity	NPC472799
0.9007	High Similarity	NPC133856
0.9007	High Similarity	NPC470675
0.9007	High Similarity	NPC202157
0.9007	High Similarity	NPC473131
0.9	High Similarity	NPC329933
0.9	High Similarity	NPC223988
0.9	High Similarity	NPC269420
0.8993	High Similarity	NPC10990
0.8993	High Similarity	NPC259632
0.8993	High Similarity	NPC21835
0.8993	High Similarity	NPC300988
0.8987	High Similarity	NPC474024
0.8986	High Similarity	NPC32470
0.8981	High Similarity	NPC469664
0.898	High Similarity	NPC202981
0.898	High Similarity	NPC223500
0.898	High Similarity	NPC64915
0.898	High Similarity	NPC166934
0.898	High Similarity	NPC10937
0.898	High Similarity	NPC161506
0.898	High Similarity	NPC159855
0.898	High Similarity	NPC1089
0.898	High Similarity	NPC107572
0.898	High Similarity	NPC228504
0.898	High Similarity	NPC166482
0.898	High Similarity	NPC66515
0.898	High Similarity	NPC227579
0.898	High Similarity	NPC169479
0.898	High Similarity	NPC148757
0.898	High Similarity	NPC76338
0.898	High Similarity	NPC324134
0.898	High Similarity	NPC306829
0.898	High Similarity	NPC78
0.898	High Similarity	NPC167624
0.898	High Similarity	NPC328164
0.898	High Similarity	NPC32739
0.898	High Similarity	NPC296917
0.898	High Similarity	NPC324436
0.898	High Similarity	NPC125855
0.898	High Similarity	NPC40833
0.898	High Similarity	NPC76372
0.898	High Similarity	NPC182852
0.898	High Similarity	NPC37496
0.898	High Similarity	NPC177354
0.898	High Similarity	NPC194432

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 NPC202595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	1013
0.2-0.3	1657
0.3-0.4	2661
0.4-0.5	1840
0.5-0.6	1011
0.6-0.7	360
0.7-0.8	145
0.8-0.85	45
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD6959	Discontinued
0.8897	High Similarity	NPD1550	Clinical (unspecified phase)
0.8897	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD7819	Suspended
0.8859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8836	High Similarity	NPD1549	Phase 2
0.8733	High Similarity	NPD2534	Approved
0.8733	High Similarity	NPD2533	Approved
0.8733	High Similarity	NPD2532	Approved
0.8701	High Similarity	NPD1934	Approved
0.863	High Similarity	NPD1510	Phase 2
0.863	High Similarity	NPD1509	Clinical (unspecified phase)
0.8621	High Similarity	NPD1607	Approved
0.859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8581	High Similarity	NPD970	Clinical (unspecified phase)
0.8571	High Similarity	NPD4380	Phase 2
0.8543	High Similarity	NPD1511	Approved
0.85	High Similarity	NPD6232	Discontinued
0.8483	Intermediate Similarity	NPD1240	Approved
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8431	Intermediate Similarity	NPD1512	Approved
0.8408	Intermediate Similarity	NPD2801	Approved
0.84	Intermediate Similarity	NPD2800	Approved
0.8397	Intermediate Similarity	NPD7411	Suspended
0.8389	Intermediate Similarity	NPD2346	Discontinued
0.8387	Intermediate Similarity	NPD3226	Approved
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD5844	Phase 1
0.8322	Intermediate Similarity	NPD2796	Approved
0.8291	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6166	Phase 2
0.8261	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3749	Approved
0.8224	Intermediate Similarity	NPD3750	Approved
0.8204	Intermediate Similarity	NPD6559	Discontinued
0.82	Intermediate Similarity	NPD6100	Approved
0.82	Intermediate Similarity	NPD1551	Phase 2
0.82	Intermediate Similarity	NPD6099	Approved
0.8187	Intermediate Similarity	NPD3882	Suspended
0.8182	Intermediate Similarity	NPD7390	Discontinued
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5711	Approved
0.816	Intermediate Similarity	NPD5710	Approved
0.8133	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8084	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7768	Phase 2
0.8072	Intermediate Similarity	NPD3818	Discontinued
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD920	Approved
0.8024	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD3817	Phase 2
0.7976	Intermediate Similarity	NPD7472	Approved
0.7961	Intermediate Similarity	NPD2935	Discontinued
0.7949	Intermediate Similarity	NPD6799	Approved
0.7929	Intermediate Similarity	NPD6797	Phase 2
0.7922	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1243	Approved
0.7905	Intermediate Similarity	NPD4625	Phase 3
0.7898	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3748	Approved
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7251	Discontinued
0.7871	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7808	Phase 3
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2344	Approved
0.7791	Intermediate Similarity	NPD5402	Approved
0.7791	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD8313	Approved
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6651	Approved
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1470	Approved
0.7748	Intermediate Similarity	NPD943	Approved
0.7733	Intermediate Similarity	NPD2313	Discontinued
0.7733	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1610	Phase 2
0.7724	Intermediate Similarity	NPD1201	Approved
0.7719	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5953	Discontinued
0.7706	Intermediate Similarity	NPD7286	Phase 2
0.7673	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7632	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1613	Approved
0.7619	Intermediate Similarity	NPD7229	Phase 3
0.7616	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4908	Phase 1
0.7598	Intermediate Similarity	NPD4363	Phase 3
0.7598	Intermediate Similarity	NPD4360	Phase 2
0.7595	Intermediate Similarity	NPD2309	Approved
0.7582	Intermediate Similarity	NPD6778	Approved
0.7582	Intermediate Similarity	NPD6781	Approved
0.7582	Intermediate Similarity	NPD6776	Approved
0.7582	Intermediate Similarity	NPD6782	Approved
0.7582	Intermediate Similarity	NPD6780	Approved
0.7582	Intermediate Similarity	NPD6779	Approved
0.7582	Intermediate Similarity	NPD230	Phase 1
0.7582	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6777	Approved
0.7578	Intermediate Similarity	NPD5403	Approved
0.7564	Intermediate Similarity	NPD1471	Phase 3
0.7562	Intermediate Similarity	NPD5401	Approved
0.7561	Intermediate Similarity	NPD37	Approved
0.7548	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD8151	Discontinued
0.7533	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.7517	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7468	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD7697	Approved
0.7459	Intermediate Similarity	NPD7696	Phase 3
0.7459	Intermediate Similarity	NPD7698	Approved
0.7458	Intermediate Similarity	NPD8150	Discontinued
0.7453	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1283	Approved
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7432	Intermediate Similarity	NPD1608	Approved
0.7419	Intermediate Similarity	NPD7871	Phase 2
0.7419	Intermediate Similarity	NPD7870	Phase 2
0.7397	Intermediate Similarity	NPD1651	Approved
0.7394	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD411	Approved
0.7386	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4361	Phase 2
0.7363	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD447	Suspended
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7341	Intermediate Similarity	NPD7177	Discontinued
0.7341	Intermediate Similarity	NPD7228	Approved
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD9717	Approved
0.7312	Intermediate Similarity	NPD6823	Phase 2
0.7312	Intermediate Similarity	NPD7003	Approved
0.7308	Intermediate Similarity	NPD6535	Approved
0.7308	Intermediate Similarity	NPD6534	Approved
0.7305	Intermediate Similarity	NPD5761	Phase 2
0.7305	Intermediate Similarity	NPD5760	Phase 2
0.7302	Intermediate Similarity	NPD7701	Phase 2
0.7301	Intermediate Similarity	NPD6273	Approved
0.7278	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD3764	Approved
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD4288	Approved
0.7255	Intermediate Similarity	NPD6832	Phase 2
0.7248	Intermediate Similarity	NPD422	Phase 1
0.7248	Intermediate Similarity	NPD1281	Approved
0.7246	Intermediate Similarity	NPD6844	Discontinued
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2798	Approved
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD17	Approved
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.719	Intermediate Similarity	NPD2861	Phase 2
0.7189	Intermediate Similarity	NPD7700	Phase 2
0.7189	Intermediate Similarity	NPD7699	Phase 2
0.7188	Intermediate Similarity	NPD7801	Approved
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD4060	Phase 1
0.7175	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2797	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