NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	1.868
LogD:	1.161
LogS:	-3.302
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	4.101
Fsp3:	0.467
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:	-4.685
MDCK Permeability:	1.7558610124979168e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.487
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	84.3833999633789%
Volume Distribution (VD):	0.755
Pgp-substrate:	12.862525939941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.258
CYP1A2-substrate:	0.563
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.542
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	13.851
Half-life (T1/2):	0.323

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.39
Carcinogencity:	0.12
Eye Corrosion:	0.007
Eye Irritation:	0.062
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC191634

Natural Product ID:	NPC191634
*Common Name:**	Leptosphaerin G
IUPAC Name:	n.a.
Synonyms:	Leptosphaerin G
Standard InCHIKey:	FDAUCSBQMOWVJY-JKNGDPHESA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-7-6-9(17)12-13(18)11-8(16)4-3-5-10(11)20-15(12,2)14(7)19/h3-5,7,14,16-17,19H,6H2,1-2H3/t7-,14+,15+/m1/s1
SMILES:	C[C@@H]1CC(=C2C(=O)c3c(cccc3O[C@]2(C)[C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098106
PubChem CID:	n.a.
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[544081]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	150000.0	nM	PMID[544081]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IC50	=	14800.0	nM	PMID[544081]

☑ 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 NPC191634 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	356
0.1-0.2	1278
0.2-0.3	3370
0.3-0.4	7979
0.4-0.5	10683
0.5-0.6	3929
0.6-0.7	5795
0.7-0.8	6786
0.8-0.85	1826
0.85-0.9	654
0.9-0.95	37
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC46564
0.9655	High Similarity	NPC207346
0.9329	High Similarity	NPC175192
0.9324	High Similarity	NPC321363
0.9324	High Similarity	NPC253904
0.9267	High Similarity	NPC164427
0.92	High Similarity	NPC326910
0.9128	High Similarity	NPC475076
0.9021	High Similarity	NPC287068
0.8986	High Similarity	NPC85773
0.8986	High Similarity	NPC473133
0.8986	High Similarity	NPC470670
0.8986	High Similarity	NPC47388
0.8968	High Similarity	NPC473961
0.8947	High Similarity	NPC237560
0.894	High Similarity	NPC275878
0.8926	High Similarity	NPC228012
0.8882	High Similarity	NPC301233
0.8874	High Similarity	NPC471677
0.8874	High Similarity	NPC471676
0.8874	High Similarity	NPC244577
0.8874	High Similarity	NPC472420
0.8874	High Similarity	NPC263384
0.8874	High Similarity	NPC472422
0.8867	High Similarity	NPC139966
0.8867	High Similarity	NPC307052
0.8859	High Similarity	NPC71055
0.8859	High Similarity	NPC91902
0.8844	High Similarity	NPC130206
0.8839	High Similarity	NPC471976
0.8836	High Similarity	NPC145673
0.8831	High Similarity	NPC477833
0.8816	High Similarity	NPC217149
0.8816	High Similarity	NPC470340
0.8816	High Similarity	NPC216035
0.8816	High Similarity	NPC474843
0.8816	High Similarity	NPC475790
0.88	High Similarity	NPC218569
0.88	High Similarity	NPC10097
0.8797	High Similarity	NPC178173
0.8792	High Similarity	NPC474302
0.8792	High Similarity	NPC469758
0.8784	High Similarity	NPC18886
0.8782	High Similarity	NPC3629
0.8774	High Similarity	NPC186113
0.8766	High Similarity	NPC10754
0.8766	High Similarity	NPC215917
0.8766	High Similarity	NPC20530
0.8758	High Similarity	NPC472583
0.8758	High Similarity	NPC7989
0.8758	High Similarity	NPC469405
0.8758	High Similarity	NPC223701
0.8758	High Similarity	NPC135522
0.875	High Similarity	NPC471229
0.875	High Similarity	NPC474021
0.875	High Similarity	NPC262039
0.875	High Similarity	NPC254412
0.875	High Similarity	NPC319910
0.875	High Similarity	NPC251144
0.875	High Similarity	NPC278476
0.875	High Similarity	NPC472636
0.875	High Similarity	NPC262038
0.875	High Similarity	NPC473131
0.875	High Similarity	NPC241874
0.875	High Similarity	NPC474023
0.875	High Similarity	NPC470675
0.875	High Similarity	NPC241387
0.8742	High Similarity	NPC237440
0.8742	High Similarity	NPC225419
0.8742	High Similarity	NPC294502
0.8742	High Similarity	NPC200221
0.8742	High Similarity	NPC270160
0.8742	High Similarity	NPC277032
0.8742	High Similarity	NPC472628
0.8733	High Similarity	NPC211466
0.8733	High Similarity	NPC122828
0.8733	High Similarity	NPC472627
0.8733	High Similarity	NPC46941
0.8733	High Similarity	NPC202494
0.8733	High Similarity	NPC21835
0.8733	High Similarity	NPC3779
0.8733	High Similarity	NPC176869
0.8733	High Similarity	NPC476182
0.8733	High Similarity	NPC472918
0.8733	High Similarity	NPC44721
0.8733	High Similarity	NPC40086
0.8725	High Similarity	NPC279417
0.8725	High Similarity	NPC4152
0.8725	High Similarity	NPC49130
0.8725	High Similarity	NPC326506
0.8725	High Similarity	NPC208176
0.8725	High Similarity	NPC469764
0.8725	High Similarity	NPC142731
0.8725	High Similarity	NPC306607
0.8725	High Similarity	NPC311144
0.8725	High Similarity	NPC62290
0.871	High Similarity	NPC472910
0.871	High Similarity	NPC474208
0.871	High Similarity	NPC474836
0.871	High Similarity	NPC472913
0.871	High Similarity	NPC475267
0.871	High Similarity	NPC48208
0.871	High Similarity	NPC472914
0.871	High Similarity	NPC245758
0.871	High Similarity	NPC472911
0.871	High Similarity	NPC162869
0.871	High Similarity	NPC96167
0.871	High Similarity	NPC222814
0.871	High Similarity	NPC156057
0.8701	High Similarity	NPC207809
0.8701	High Similarity	NPC37392
0.8701	High Similarity	NPC472909
0.8701	High Similarity	NPC68727
0.8701	High Similarity	NPC259710
0.8701	High Similarity	NPC304207
0.8701	High Similarity	NPC477958
0.8701	High Similarity	NPC48579
0.8701	High Similarity	NPC217706
0.8699	High Similarity	NPC268691
0.8699	High Similarity	NPC18457
0.8693	High Similarity	NPC35567
0.8693	High Similarity	NPC161881
0.8693	High Similarity	NPC470338
0.8693	High Similarity	NPC473996
0.8693	High Similarity	NPC171651
0.8693	High Similarity	NPC10807
0.8693	High Similarity	NPC268992
0.8693	High Similarity	NPC210597
0.8693	High Similarity	NPC113608
0.8693	High Similarity	NPC470337
0.8693	High Similarity	NPC150123
0.8693	High Similarity	NPC244583
0.8693	High Similarity	NPC51824
0.8693	High Similarity	NPC256141
0.8693	High Similarity	NPC167903
0.8693	High Similarity	NPC138288
0.8693	High Similarity	NPC56232
0.8693	High Similarity	NPC281272
0.8693	High Similarity	NPC75069
0.8693	High Similarity	NPC243171
0.8684	High Similarity	NPC267117
0.8684	High Similarity	NPC105136
0.8671	High Similarity	NPC476931
0.8667	High Similarity	NPC472629
0.8667	High Similarity	NPC1940
0.8667	High Similarity	NPC148011
0.8667	High Similarity	NPC299011
0.8667	High Similarity	NPC209278
0.8662	High Similarity	NPC476929
0.8658	High Similarity	NPC255133
0.8658	High Similarity	NPC113770
0.8658	High Similarity	NPC95751
0.8658	High Similarity	NPC242100
0.8654	High Similarity	NPC329091
0.8654	High Similarity	NPC152904
0.8654	High Similarity	NPC470339
0.8649	High Similarity	NPC150023
0.8645	High Similarity	NPC317383
0.8645	High Similarity	NPC78492
0.8645	High Similarity	NPC24640
0.8645	High Similarity	NPC235165
0.8645	High Similarity	NPC208152
0.8645	High Similarity	NPC255106
0.8645	High Similarity	NPC154341
0.8645	High Similarity	NPC201837
0.8639	High Similarity	NPC469523
0.8636	High Similarity	NPC209760
0.8636	High Similarity	NPC293286
0.8636	High Similarity	NPC203080
0.8636	High Similarity	NPC155686
0.8636	High Similarity	NPC18727
0.8636	High Similarity	NPC100134
0.8636	High Similarity	NPC248793
0.8636	High Similarity	NPC180301
0.8627	High Similarity	NPC204515
0.8627	High Similarity	NPC190217
0.8627	High Similarity	NPC46882
0.8627	High Similarity	NPC472580
0.8627	High Similarity	NPC474744
0.8627	High Similarity	NPC132990
0.8627	High Similarity	NPC39819
0.8627	High Similarity	NPC70016
0.8627	High Similarity	NPC472423
0.8627	High Similarity	NPC215921
0.8627	High Similarity	NPC328740
0.8627	High Similarity	NPC289774
0.8627	High Similarity	NPC471675
0.8627	High Similarity	NPC477897
0.8627	High Similarity	NPC474772
0.8627	High Similarity	NPC209846
0.8618	High Similarity	NPC89442
0.8609	High Similarity	NPC308200
0.8608	High Similarity	NPC472402
0.8608	High Similarity	NPC472964
0.86	High Similarity	NPC131568
0.86	High Similarity	NPC131579
0.86	High Similarity	NPC303185
0.86	High Similarity	NPC316535
0.86	High Similarity	NPC212697
0.86	High Similarity	NPC87486

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 NPC191634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	824
0.2-0.3	1682
0.3-0.4	2580
0.4-0.5	1970
0.5-0.6	1110
0.6-0.7	483
0.7-0.8	155
0.8-0.85	22
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD1934	Approved
0.8516	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1549	Phase 2
0.8442	Intermediate Similarity	NPD4380	Phase 2
0.8397	Intermediate Similarity	NPD2801	Approved
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5402	Approved
0.8272	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD7075	Discontinued
0.8235	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1511	Approved
0.8165	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5403	Approved
0.8121	Intermediate Similarity	NPD1510	Phase 2
0.8113	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6559	Discontinued
0.8072	Intermediate Similarity	NPD7074	Phase 3
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.8067	Intermediate Similarity	NPD2796	Approved
0.8065	Intermediate Similarity	NPD1512	Approved
0.8063	Intermediate Similarity	NPD3882	Suspended
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD1607	Approved
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7974	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1240	Approved
0.7964	Intermediate Similarity	NPD7472	Approved
0.7961	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6099	Approved
0.7947	Intermediate Similarity	NPD6100	Approved
0.7937	Intermediate Similarity	NPD7819	Suspended
0.7935	Intermediate Similarity	NPD6799	Approved
0.7929	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6797	Phase 2
0.7888	Intermediate Similarity	NPD3817	Phase 2
0.7885	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7251	Discontinued
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.7857	Intermediate Similarity	NPD3750	Approved
0.7824	Intermediate Similarity	NPD7808	Phase 3
0.7812	Intermediate Similarity	NPD7411	Suspended
0.7798	Intermediate Similarity	NPD5844	Phase 1
0.7792	Intermediate Similarity	NPD2800	Approved
0.7784	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD8313	Approved
0.7778	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7738	Intermediate Similarity	NPD3751	Discontinued
0.7733	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD4749	Approved
0.7718	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6232	Discontinued
0.7708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3749	Approved
0.7682	Intermediate Similarity	NPD447	Suspended
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7644	Intermediate Similarity	NPD8434	Phase 2
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD7768	Phase 2
0.7605	Intermediate Similarity	NPD3787	Discontinued
0.7602	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2935	Discontinued
0.7578	Intermediate Similarity	NPD3226	Approved
0.7543	Intermediate Similarity	NPD8150	Discontinued
0.7534	Intermediate Similarity	NPD9717	Approved
0.7532	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD2424	Discontinued
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7469	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4908	Phase 1
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7453	Intermediate Similarity	NPD920	Approved
0.7452	Intermediate Similarity	NPD1652	Phase 2
0.7451	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5124	Phase 1
0.744	Intermediate Similarity	NPD1247	Approved
0.7439	Intermediate Similarity	NPD6844	Discontinued
0.7438	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7407	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD943	Approved
0.7377	Intermediate Similarity	NPD6782	Approved
0.7377	Intermediate Similarity	NPD6776	Approved
0.7377	Intermediate Similarity	NPD6778	Approved
0.7377	Intermediate Similarity	NPD6779	Approved
0.7377	Intermediate Similarity	NPD6781	Approved
0.7377	Intermediate Similarity	NPD6777	Approved
0.7377	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD411	Approved
0.7351	Intermediate Similarity	NPD6832	Phase 2
0.7347	Intermediate Similarity	NPD1091	Approved
0.7342	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD230	Phase 1
0.7333	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7314	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4966	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD4965	Approved
0.7303	Intermediate Similarity	NPD3027	Phase 3
0.7297	Intermediate Similarity	NPD6823	Phase 2
0.7294	Intermediate Similarity	NPD5711	Approved
0.7294	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5761	Phase 2
0.7289	Intermediate Similarity	NPD5760	Phase 2
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD1470	Approved
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7255	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD1243	Approved
0.723	Intermediate Similarity	NPD1201	Approved
0.723	Intermediate Similarity	NPD422	Phase 1
0.7226	Intermediate Similarity	NPD1933	Approved
0.7226	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD4662	Approved
0.7222	Intermediate Similarity	NPD4661	Approved
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD5647	Approved
0.7219	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD919	Approved
0.7215	Intermediate Similarity	NPD2344	Approved
0.7209	Intermediate Similarity	NPD2403	Approved
0.7205	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5953	Discontinued
0.7198	Intermediate Similarity	NPD4363	Phase 3
0.7198	Intermediate Similarity	NPD4360	Phase 2
0.7197	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1548	Phase 1
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7286	Phase 2
0.7172	Intermediate Similarity	NPD9493	Approved
0.7171	Intermediate Similarity	NPD2861	Phase 2
0.7166	Intermediate Similarity	NPD7698	Approved
0.7166	Intermediate Similarity	NPD7696	Phase 3
0.7166	Intermediate Similarity	NPD7697	Approved
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7128	Intermediate Similarity	NPD7871	Phase 2
0.7128	Intermediate Similarity	NPD7870	Phase 2
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD6004	Phase 3
0.7107	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6005	Phase 3
0.7107	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6002	Phase 3
0.7105	Intermediate Similarity	NPD7701	Phase 2
0.7104	Intermediate Similarity	NPD6534	Approved
0.7104	Intermediate Similarity	NPD6535	Approved
0.7103	Intermediate Similarity	NPD6671	Approved
0.7099	Intermediate Similarity	NPD3300	Phase 2
0.7097	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD7783	Phase 2
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7801	Approved
0.7067	Intermediate Similarity	NPD1608	Approved
0.7055	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7390	Discontinued
0.7053	Intermediate Similarity	NPD7584	Approved
0.7051	Intermediate Similarity	NPD4307	Phase 2
0.7048	Intermediate Similarity	NPD2651	Approved
0.7048	Intermediate Similarity	NPD2649	Approved
0.7037	Intermediate Similarity	NPD2309	Approved
0.7037	Intermediate Similarity	NPD6190	Approved
0.7031	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7874	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