NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	278.135
LogP:	1.605
LogD:	1.139
LogS:	-1.833
# Rotatable Bonds:	4
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	3.733
Fsp3:	0.6
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:	-4.612
MDCK Permeability:	3.383160583325662e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.443
Plasma Protein Binding (PPB):	39.16769790649414%
Volume Distribution (VD):	1.127
Pgp-substrate:	56.12491226196289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.502
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.681
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	6.557
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.163
Carcinogencity:	0.294
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC469385

Natural Product ID:	NPC469385
*Common Name:**	Ustusorane A
IUPAC Name:	7-(hydroxymethyl)-6-(2-hydroxypropyl)-2-propan-2-ylidene-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	FYUKKVDWTSHXKN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-8(2)14-13(18)11-5-4-10(6-9(3)17)12(7-16)15(11)19-14/h4-5,9,16-17H,6-7H2,1-3H3
SMILES:	CC(CC1=C(C2=C(C=C1)C(=O)C(=C(C)C)O2)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077457
PubChem CID:	44557644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[506226]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[506226]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	130.0	nM	PMID[506227]

☑ 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 NPC469385 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	351
0.1-0.2	1398
0.2-0.3	3400
0.3-0.4	8355
0.4-0.5	10615
0.5-0.6	3982
0.6-0.7	6980
0.7-0.8	6766
0.8-0.85	804
0.85-0.9	34
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC469425
0.9514	High Similarity	NPC175617
0.9448	High Similarity	NPC471349
0.9448	High Similarity	NPC471347
0.9065	High Similarity	NPC217914
0.9041	High Similarity	NPC219560
0.9034	High Similarity	NPC471346
0.898	High Similarity	NPC228906
0.898	High Similarity	NPC471348
0.898	High Similarity	NPC469416
0.8881	High Similarity	NPC477537
0.8824	High Similarity	NPC313368
0.875	High Similarity	NPC477535
0.8741	High Similarity	NPC98395
0.8707	High Similarity	NPC474630
0.8681	High Similarity	NPC477408
0.8639	High Similarity	NPC477409
0.8621	High Similarity	NPC37206
0.8599	High Similarity	NPC316262
0.8599	High Similarity	NPC314653
0.8591	High Similarity	NPC71055
0.8571	High Similarity	NPC104380
0.8571	High Similarity	NPC217602
0.8571	High Similarity	NPC473282
0.8552	High Similarity	NPC268691
0.8542	High Similarity	NPC477534
0.8526	High Similarity	NPC472780
0.8526	High Similarity	NPC472783
0.8526	High Similarity	NPC269117
0.8523	High Similarity	NPC470357
0.8503	High Similarity	NPC171870
0.85	High Similarity	NPC313717
0.85	High Similarity	NPC315306
0.8497	Intermediate Similarity	NPC193200
0.8493	Intermediate Similarity	NPC137009
0.8487	Intermediate Similarity	NPC72958
0.8487	Intermediate Similarity	NPC232645
0.8477	Intermediate Similarity	NPC226578
0.8467	Intermediate Similarity	NPC8817
0.8467	Intermediate Similarity	NPC137296
0.8462	Intermediate Similarity	NPC472782
0.8462	Intermediate Similarity	NPC472781
0.8456	Intermediate Similarity	NPC28632
0.8452	Intermediate Similarity	NPC212967
0.8452	Intermediate Similarity	NPC164110
0.8452	Intermediate Similarity	NPC246647
0.8452	Intermediate Similarity	NPC294300
0.8452	Intermediate Similarity	NPC96342
0.8452	Intermediate Similarity	NPC476404
0.8452	Intermediate Similarity	NPC317900
0.8435	Intermediate Similarity	NPC283292
0.8431	Intermediate Similarity	NPC275878
0.8431	Intermediate Similarity	NPC40356
0.8431	Intermediate Similarity	NPC87708
0.8431	Intermediate Similarity	NPC154683
0.8431	Intermediate Similarity	NPC271681
0.8421	Intermediate Similarity	NPC202595
0.8411	Intermediate Similarity	NPC5537
0.8411	Intermediate Similarity	NPC73411
0.8411	Intermediate Similarity	NPC215711
0.84	Intermediate Similarity	NPC300540
0.8392	Intermediate Similarity	NPC477536
0.8389	Intermediate Similarity	NPC471451
0.8389	Intermediate Similarity	NPC475813
0.8387	Intermediate Similarity	NPC180924
0.838	Intermediate Similarity	NPC324488
0.8378	Intermediate Similarity	NPC329493
0.8378	Intermediate Similarity	NPC96692
0.8377	Intermediate Similarity	NPC290927
0.8377	Intermediate Similarity	NPC135522
0.8377	Intermediate Similarity	NPC210942
0.8377	Intermediate Similarity	NPC169990
0.8377	Intermediate Similarity	NPC301233
0.8377	Intermediate Similarity	NPC84721
0.8369	Intermediate Similarity	NPC939
0.8366	Intermediate Similarity	NPC478148
0.8366	Intermediate Similarity	NPC149526
0.8366	Intermediate Similarity	NPC470569
0.8366	Intermediate Similarity	NPC258249
0.8366	Intermediate Similarity	NPC471613
0.8366	Intermediate Similarity	NPC474417
0.8365	Intermediate Similarity	NPC472784
0.8355	Intermediate Similarity	NPC97028
0.8355	Intermediate Similarity	NPC158338
0.8355	Intermediate Similarity	NPC97029
0.8355	Intermediate Similarity	NPC100985
0.8355	Intermediate Similarity	NPC288036
0.8355	Intermediate Similarity	NPC65589
0.8345	Intermediate Similarity	NPC232996
0.8344	Intermediate Similarity	NPC210320
0.8344	Intermediate Similarity	NPC22005
0.8344	Intermediate Similarity	NPC470810
0.8344	Intermediate Similarity	NPC7943
0.8344	Intermediate Similarity	NPC284495
0.8344	Intermediate Similarity	NPC123202
0.8333	Intermediate Similarity	NPC281137
0.8333	Intermediate Similarity	NPC282390
0.8333	Intermediate Similarity	NPC247743
0.8333	Intermediate Similarity	NPC75694
0.8323	Intermediate Similarity	NPC148938
0.8322	Intermediate Similarity	NPC84266
0.8322	Intermediate Similarity	NPC309430
0.8322	Intermediate Similarity	NPC470160
0.8322	Intermediate Similarity	NPC162476
0.8322	Intermediate Similarity	NPC130206
0.8313	Intermediate Similarity	NPC191012
0.8312	Intermediate Similarity	NPC253904
0.8312	Intermediate Similarity	NPC473967
0.8312	Intermediate Similarity	NPC321363
0.8312	Intermediate Similarity	NPC273483
0.8311	Intermediate Similarity	NPC149533
0.8302	Intermediate Similarity	NPC100849
0.8301	Intermediate Similarity	NPC61258
0.8301	Intermediate Similarity	NPC290954
0.8301	Intermediate Similarity	NPC158866
0.8301	Intermediate Similarity	NPC470568
0.8301	Intermediate Similarity	NPC255641
0.8299	Intermediate Similarity	NPC1268
0.8291	Intermediate Similarity	NPC117985
0.8291	Intermediate Similarity	NPC24761
0.8289	Intermediate Similarity	NPC27221
0.8289	Intermediate Similarity	NPC7025
0.8289	Intermediate Similarity	NPC256672
0.8289	Intermediate Similarity	NPC168085
0.8289	Intermediate Similarity	NPC37139
0.828	Intermediate Similarity	NPC186113
0.8278	Intermediate Similarity	NPC469758
0.8278	Intermediate Similarity	NPC130176
0.8278	Intermediate Similarity	NPC99454
0.8276	Intermediate Similarity	NPC142027
0.8276	Intermediate Similarity	NPC27407
0.8276	Intermediate Similarity	NPC164136
0.8267	Intermediate Similarity	NPC245482
0.8267	Intermediate Similarity	NPC105381
0.8267	Intermediate Similarity	NPC274085
0.8267	Intermediate Similarity	NPC10302
0.8267	Intermediate Similarity	NPC89664
0.8267	Intermediate Similarity	NPC301751
0.8264	Intermediate Similarity	NPC254603
0.8261	Intermediate Similarity	NPC150131
0.8258	Intermediate Similarity	NPC189130
0.8258	Intermediate Similarity	NPC329844
0.8258	Intermediate Similarity	NPC235333
0.8255	Intermediate Similarity	NPC182255
0.8255	Intermediate Similarity	NPC474385
0.8255	Intermediate Similarity	NPC94076
0.8252	Intermediate Similarity	NPC205360
0.8247	Intermediate Similarity	NPC230848
0.8247	Intermediate Similarity	NPC472423
0.8247	Intermediate Similarity	NPC474772
0.8247	Intermediate Similarity	NPC474744
0.8247	Intermediate Similarity	NPC39819
0.8243	Intermediate Similarity	NPC139554
0.8243	Intermediate Similarity	NPC165172
0.8239	Intermediate Similarity	NPC216752
0.8239	Intermediate Similarity	NPC475106
0.8235	Intermediate Similarity	NPC269420
0.8235	Intermediate Similarity	NPC65775
0.8235	Intermediate Similarity	NPC198927
0.8235	Intermediate Similarity	NPC10027
0.8235	Intermediate Similarity	NPC233267
0.8235	Intermediate Similarity	NPC317492
0.8235	Intermediate Similarity	NPC70764
0.8235	Intermediate Similarity	NPC39929
0.8235	Intermediate Similarity	NPC296030
0.8235	Intermediate Similarity	NPC470461
0.8235	Intermediate Similarity	NPC291049
0.8228	Intermediate Similarity	NPC472961
0.8228	Intermediate Similarity	NPC472962
0.8228	Intermediate Similarity	NPC472618
0.8227	Intermediate Similarity	NPC469386
0.8224	Intermediate Similarity	NPC252208
0.8224	Intermediate Similarity	NPC202494
0.8224	Intermediate Similarity	NPC14098
0.8224	Intermediate Similarity	NPC66991
0.8224	Intermediate Similarity	NPC478163
0.8224	Intermediate Similarity	NPC472036
0.8224	Intermediate Similarity	NPC259632
0.8219	Intermediate Similarity	NPC84699
0.8219	Intermediate Similarity	NPC141934
0.8217	Intermediate Similarity	NPC201127
0.8212	Intermediate Similarity	NPC478019
0.8212	Intermediate Similarity	NPC472034
0.8212	Intermediate Similarity	NPC470857
0.8212	Intermediate Similarity	NPC297788
0.8212	Intermediate Similarity	NPC87486
0.8212	Intermediate Similarity	NPC469764
0.8212	Intermediate Similarity	NPC124780
0.821	Intermediate Similarity	NPC473096
0.821	Intermediate Similarity	NPC473095
0.8205	Intermediate Similarity	NPC478159
0.8205	Intermediate Similarity	NPC326910
0.8205	Intermediate Similarity	NPC213936
0.8205	Intermediate Similarity	NPC478161
0.8205	Intermediate Similarity	NPC237560
0.8205	Intermediate Similarity	NPC99381
0.8205	Intermediate Similarity	NPC297531
0.82	Intermediate Similarity	NPC469885
0.82	Intermediate Similarity	NPC1534
0.82	Intermediate Similarity	NPC469542

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 NPC469385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	917
0.2-0.3	1609
0.3-0.4	2543
0.4-0.5	2011
0.5-0.6	1138
0.6-0.7	450
0.7-0.8	159
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8141	Intermediate Similarity	NPD7819	Suspended
0.8117	Intermediate Similarity	NPD3226	Approved
0.8108	Intermediate Similarity	NPD2346	Discontinued
0.8092	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD3882	Suspended
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7962	Intermediate Similarity	NPD6801	Discontinued
0.795	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD6599	Discontinued
0.7933	Intermediate Similarity	NPD1549	Phase 2
0.7911	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1471	Phase 3
0.7867	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1607	Approved
0.7815	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD411	Approved
0.78	Intermediate Similarity	NPD1551	Phase 2
0.78	Intermediate Similarity	NPD2796	Approved
0.7792	Intermediate Similarity	NPD6799	Approved
0.7763	Intermediate Similarity	NPD2800	Approved
0.7756	Intermediate Similarity	NPD5403	Approved
0.775	Intermediate Similarity	NPD5402	Approved
0.775	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD9717	Approved
0.7742	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD1510	Phase 2
0.7722	Intermediate Similarity	NPD4380	Phase 2
0.7716	Intermediate Similarity	NPD919	Approved
0.7712	Intermediate Similarity	NPD4628	Phase 3
0.7703	Intermediate Similarity	NPD1240	Approved
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7673	Intermediate Similarity	NPD7411	Suspended
0.7669	Intermediate Similarity	NPD5494	Approved
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6005	Phase 3
0.7632	Intermediate Similarity	NPD6004	Phase 3
0.7632	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6002	Phase 3
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5401	Approved
0.7625	Intermediate Similarity	NPD1934	Approved
0.7622	Intermediate Similarity	NPD1247	Approved
0.7616	Intermediate Similarity	NPD2799	Discontinued
0.759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1512	Approved
0.7576	Intermediate Similarity	NPD5710	Approved
0.7576	Intermediate Similarity	NPD5711	Approved
0.7568	Intermediate Similarity	NPD2313	Discontinued
0.756	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8312	Approved
0.7544	Intermediate Similarity	NPD8313	Approved
0.7533	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD920	Approved
0.7532	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3750	Approved
0.747	Intermediate Similarity	NPD6232	Discontinued
0.7466	Intermediate Similarity	NPD1470	Approved
0.7466	Intermediate Similarity	NPD1203	Approved
0.7452	Intermediate Similarity	NPD1511	Approved
0.7451	Intermediate Similarity	NPD6099	Approved
0.7451	Intermediate Similarity	NPD6100	Approved
0.744	Intermediate Similarity	NPD7473	Discontinued
0.7439	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6832	Phase 2
0.7431	Intermediate Similarity	NPD1201	Approved
0.7413	Intermediate Similarity	NPD1778	Approved
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5762	Approved
0.7403	Intermediate Similarity	NPD5763	Approved
0.7403	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7381	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6797	Phase 2
0.7362	Intermediate Similarity	NPD2801	Approved
0.7362	Intermediate Similarity	NPD5760	Phase 2
0.7362	Intermediate Similarity	NPD5761	Phase 2
0.7358	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD5405	Approved
0.7338	Intermediate Similarity	NPD5406	Approved
0.7338	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD5404	Approved
0.7326	Intermediate Similarity	NPD7251	Discontinued
0.7325	Intermediate Similarity	NPD2309	Approved
0.7321	Intermediate Similarity	NPD3926	Phase 2
0.7314	Intermediate Similarity	NPD8434	Phase 2
0.7314	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1019	Discontinued
0.7297	Intermediate Similarity	NPD2798	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7294	Intermediate Similarity	NPD7177	Discontinued
0.7292	Intermediate Similarity	NPD4626	Approved
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7808	Phase 3
0.7279	Intermediate Similarity	NPD6696	Suspended
0.7273	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.726	Intermediate Similarity	NPD1608	Approved
0.7255	Intermediate Similarity	NPD6651	Approved
0.7254	Intermediate Similarity	NPD9493	Approved
0.7253	Intermediate Similarity	NPD6777	Approved
0.7253	Intermediate Similarity	NPD6780	Approved
0.7253	Intermediate Similarity	NPD6781	Approved
0.7253	Intermediate Similarity	NPD6776	Approved
0.7253	Intermediate Similarity	NPD6778	Approved
0.7253	Intermediate Similarity	NPD6779	Approved
0.7253	Intermediate Similarity	NPD6782	Approved
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7228	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD1651	Approved
0.7222	Intermediate Similarity	NPD5691	Approved
0.7219	Intermediate Similarity	NPD3268	Approved
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7186	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1283	Approved
0.7161	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7152	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD7054	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7697	Approved
0.7133	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7390	Discontinued
0.7114	Intermediate Similarity	NPD2797	Approved
0.711	Intermediate Similarity	NPD7472	Approved
0.7105	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7870	Phase 2
0.7097	Intermediate Similarity	NPD7871	Phase 2
0.7093	Intermediate Similarity	NPD2163	Approved
0.7091	Intermediate Similarity	NPD6844	Discontinued
0.7089	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6534	Approved
0.7072	Intermediate Similarity	NPD6535	Approved
0.7069	Intermediate Similarity	NPD5953	Discontinued
0.7067	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD17	Approved
0.7042	Intermediate Similarity	NPD1241	Discontinued
0.7034	Intermediate Similarity	NPD9545	Approved
0.7027	Intermediate Similarity	NPD3972	Approved
0.7025	Intermediate Similarity	NPD2424	Discontinued
0.7018	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4307	Phase 2
0.7012	Intermediate Similarity	NPD7458	Discontinued
0.7012	Intermediate Similarity	NPD2651	Approved
0.7012	Intermediate Similarity	NPD2649	Approved
0.7011	Intermediate Similarity	NPD1729	Discontinued
0.7006	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD3764	Approved
0.6988	Remote Similarity	NPD37	Approved
0.6984	Remote Similarity	NPD7701	Phase 2
0.6981	Remote Similarity	NPD2654	Approved
0.698	Remote Similarity	NPD4749	Approved
0.6975	Remote Similarity	NPD4662	Approved
0.6975	Remote Similarity	NPD4661	Approved
0.6971	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5124	Phase 1
0.6968	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4965	Approved
0.6964	Remote Similarity	NPD4967	Phase 2
0.6964	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD7229	Phase 3
0.6959	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD7699	Phase 2
0.6957	Remote Similarity	NPD7700	Phase 2
0.6954	Remote Similarity	NPD5647	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