NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	270.225
LogP:	3.378
LogD:	2.946
LogS:	-4.27
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	2.24
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.798
MDCK Permeability:	1.62291107699275e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	94.55855560302734%
Volume Distribution (VD):	0.82
Pgp-substrate:	5.154942035675049%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.708
CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.59
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.536
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	8.389
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.514
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.704
Carcinogencity:	0.099
Eye Corrosion:	0.027
Eye Irritation:	0.966
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC84266

Natural Product ID:	NPC84266
*Common Name:**	1-(1-Hydroxy-6,8-Dimethoxy-3-Methylnaphthalen-2-Yl)Ethanone
IUPAC Name:	1-(1-hydroxy-6,8-dimethoxy-3-methylnaphthalen-2-yl)ethanone
Synonyms:
Standard InCHIKey:	FHHUIFBQMMGHQW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-8-5-10-6-11(18-3)7-12(19-4)14(10)15(17)13(8)9(2)16/h5-7,17H,1-4H3
SMILES:	Cc1cc2cc(cc(c2c(c1C(=O)C)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3355661
PubChem CID:	12478854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

*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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[17345316]
NPO3206	Karwinskia parvifolia	Species	Rhamnaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25402632]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2140	Botryococcus braunii	Species	Botryococcaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7706	Bartlettina karwinskiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2140	Botryococcus braunii	Species	Botryococcaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9708	Aster verticillatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3206	Karwinskia parvifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3035	Karwinskia humboldtiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9402	Morus mongolica	Species	Moraceae	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[476282]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[476282]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9600.0	nM	PMID[476282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[476282]

☑ 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 NPC84266 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	392
0.1-0.2	1746
0.2-0.3	4008
0.3-0.4	10864
0.4-0.5	7468
0.5-0.6	3760
0.6-0.7	5443
0.7-0.8	5444
0.8-0.85	2337
0.85-0.9	1039
0.9-0.95	181
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC94076
0.9926	High Similarity	NPC182255
0.9714	High Similarity	NPC34802
0.9577	High Similarity	NPC65589
0.9577	High Similarity	NPC100985
0.9577	High Similarity	NPC97028
0.9577	High Similarity	NPC288036
0.9577	High Similarity	NPC97029
0.9577	High Similarity	NPC329933
0.9577	High Similarity	NPC158338
0.9574	High Similarity	NPC123202
0.9574	High Similarity	NPC22005
0.9574	High Similarity	NPC7943
0.9507	High Similarity	NPC27221
0.9507	High Similarity	NPC256672
0.9507	High Similarity	NPC7025
0.9504	High Similarity	NPC163846
0.9504	High Similarity	NPC225173
0.9444	High Similarity	NPC232645
0.9444	High Similarity	NPC149526
0.9444	High Similarity	NPC72958
0.9444	High Similarity	NPC474417
0.9437	High Similarity	NPC190648
0.9437	High Similarity	NPC56433
0.9437	High Similarity	NPC289042
0.9437	High Similarity	NPC312929
0.9437	High Similarity	NPC126767
0.9437	High Similarity	NPC125801
0.9437	High Similarity	NPC245584
0.9437	High Similarity	NPC118027
0.9379	High Similarity	NPC87708
0.9375	High Similarity	NPC470568
0.9375	High Similarity	NPC325983
0.9362	High Similarity	NPC19896
0.9357	High Similarity	NPC49108
0.9353	High Similarity	NPC165172
0.9353	High Similarity	NPC472366
0.9315	High Similarity	NPC169990
0.9315	High Similarity	NPC329844
0.9315	High Similarity	NPC210942
0.931	High Similarity	NPC478148
0.931	High Similarity	NPC470569
0.9306	High Similarity	NPC291049
0.9306	High Similarity	NPC233267
0.9252	High Similarity	NPC66508
0.9252	High Similarity	NPC226656
0.9247	High Similarity	NPC40356
0.9247	High Similarity	NPC154683
0.9241	High Similarity	NPC147735
0.9241	High Similarity	NPC290954
0.9241	High Similarity	NPC294646
0.9241	High Similarity	NPC255641
0.9241	High Similarity	NPC202595
0.9241	High Similarity	NPC119929
0.9236	High Similarity	NPC2569
0.9236	High Similarity	NPC105415
0.9236	High Similarity	NPC172329
0.9225	High Similarity	NPC189650
0.922	High Similarity	NPC250755
0.922	High Similarity	NPC126534
0.922	High Similarity	NPC232021
0.922	High Similarity	NPC40118
0.9214	High Similarity	NPC109232
0.9203	High Similarity	NPC13575
0.9189	High Similarity	NPC180924
0.9184	High Similarity	NPC93552
0.9178	High Similarity	NPC258249
0.9178	High Similarity	NPC133856
0.9161	High Similarity	NPC28632
0.9155	High Similarity	NPC310340
0.9155	High Similarity	NPC297600
0.9155	High Similarity	NPC167663
0.9149	High Similarity	NPC275734
0.9149	High Similarity	NPC265178
0.9149	High Similarity	NPC11056
0.9143	High Similarity	NPC21350
0.9143	High Similarity	NPC472368
0.9137	High Similarity	NPC66349
0.9137	High Similarity	NPC41461
0.9137	High Similarity	NPC472367
0.9137	High Similarity	NPC98115
0.9137	High Similarity	NPC150399
0.9137	High Similarity	NPC477243
0.9137	High Similarity	NPC477242
0.9137	High Similarity	NPC249606
0.9137	High Similarity	NPC1486
0.9137	High Similarity	NPC12165
0.9137	High Similarity	NPC473391
0.9137	High Similarity	NPC477244
0.9137	High Similarity	NPC274109
0.9137	High Similarity	NPC472364
0.9137	High Similarity	NPC168105
0.9137	High Similarity	NPC476333
0.9137	High Similarity	NPC186838
0.9137	High Similarity	NPC25287
0.913	High Similarity	NPC103842
0.9128	High Similarity	NPC212967
0.9128	High Similarity	NPC96342
0.9128	High Similarity	NPC246647
0.9128	High Similarity	NPC164110
0.9116	High Similarity	NPC175978
0.9116	High Similarity	NPC273483
0.9116	High Similarity	NPC217447
0.9097	High Similarity	NPC473927
0.9078	High Similarity	NPC168471
0.9078	High Similarity	NPC477956
0.9071	High Similarity	NPC317119
0.9071	High Similarity	NPC472419
0.9071	High Similarity	NPC153979
0.9067	High Similarity	NPC324736
0.9065	High Similarity	NPC158481
0.9065	High Similarity	NPC156092
0.9065	High Similarity	NPC131039
0.9058	High Similarity	NPC159623
0.9058	High Similarity	NPC144051
0.9058	High Similarity	NPC28753
0.9058	High Similarity	NPC294593
0.9058	High Similarity	NPC82225
0.9058	High Similarity	NPC18877
0.9058	High Similarity	NPC204960
0.9058	High Similarity	NPC20560
0.9054	High Similarity	NPC107109
0.9054	High Similarity	NPC208806
0.9051	High Similarity	NPC27490
0.9044	High Similarity	NPC84772
0.9041	High Similarity	NPC65775
0.9041	High Similarity	NPC80370
0.9041	High Similarity	NPC10027
0.9028	High Similarity	NPC49282
0.9028	High Similarity	NPC134621
0.9028	High Similarity	NPC34482
0.9014	High Similarity	NPC204985
0.9014	High Similarity	NPC215311
0.9014	High Similarity	NPC213659
0.9014	High Similarity	NPC144118
0.9014	High Similarity	NPC80962
0.9014	High Similarity	NPC326109
0.9014	High Similarity	NPC219917
0.9014	High Similarity	NPC110810
0.9014	High Similarity	NPC253822
0.9014	High Similarity	NPC259166
0.9014	High Similarity	NPC48624
0.9014	High Similarity	NPC172250
0.9007	High Similarity	NPC472052
0.9007	High Similarity	NPC243528
0.9007	High Similarity	NPC251681
0.9007	High Similarity	NPC472060
0.9007	High Similarity	NPC186325
0.9007	High Similarity	NPC470342
0.9	High Similarity	NPC24394
0.9	High Similarity	NPC37543
0.9	High Similarity	NPC213603
0.9	High Similarity	NPC193792
0.9	High Similarity	NPC199463
0.9	High Similarity	NPC263483
0.8993	High Similarity	NPC148938
0.8993	High Similarity	NPC89625
0.8993	High Similarity	NPC180905
0.8993	High Similarity	NPC182496
0.8993	High Similarity	NPC286336
0.8993	High Similarity	NPC149618
0.8986	High Similarity	NPC215875
0.8986	High Similarity	NPC267205
0.8986	High Similarity	NPC15834
0.898	High Similarity	NPC158866
0.898	High Similarity	NPC227122
0.8978	High Similarity	NPC324482
0.8973	High Similarity	NPC37139
0.8973	High Similarity	NPC216624
0.8973	High Similarity	NPC472841
0.8971	High Similarity	NPC230818
0.8966	High Similarity	NPC237208
0.8966	High Similarity	NPC267509
0.8966	High Similarity	NPC196114
0.8966	High Similarity	NPC470570
0.8966	High Similarity	NPC24136
0.8966	High Similarity	NPC187282
0.8966	High Similarity	NPC138978
0.8966	High Similarity	NPC290133
0.8966	High Similarity	NPC99454
0.8966	High Similarity	NPC130176
0.8958	High Similarity	NPC95123
0.8958	High Similarity	NPC21599
0.8958	High Similarity	NPC475201
0.8958	High Similarity	NPC48762
0.8958	High Similarity	NPC193703
0.8958	High Similarity	NPC66404
0.8951	High Similarity	NPC470087
0.8951	High Similarity	NPC26051
0.8951	High Similarity	NPC470089
0.8951	High Similarity	NPC18714
0.8951	High Similarity	NPC55832
0.8951	High Similarity	NPC469404
0.8951	High Similarity	NPC321980
0.8951	High Similarity	NPC52789
0.8951	High Similarity	NPC103752
0.8951	High Similarity	NPC268204
0.8947	High Similarity	NPC189552
0.8947	High Similarity	NPC273467
0.8947	High Similarity	NPC66288

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 NPC84266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1031
0.2-0.3	1535
0.3-0.4	2682
0.4-0.5	1840
0.5-0.6	1093
0.6-0.7	411
0.7-0.8	154
0.8-0.85	26
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD1607	Approved
0.8913	High Similarity	NPD1240	Approved
0.8873	High Similarity	NPD970	Clinical (unspecified phase)
0.8824	High Similarity	NPD6959	Discontinued
0.8794	High Similarity	NPD1509	Clinical (unspecified phase)
0.8794	High Similarity	NPD1510	Phase 2
0.8767	High Similarity	NPD4378	Clinical (unspecified phase)
0.8767	High Similarity	NPD2533	Approved
0.8767	High Similarity	NPD2532	Approved
0.8767	High Similarity	NPD2534	Approved
0.8766	High Similarity	NPD6232	Discontinued
0.8718	High Similarity	NPD7473	Discontinued
0.8675	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD7390	Discontinued
0.8553	High Similarity	NPD2393	Clinical (unspecified phase)
0.8542	High Similarity	NPD1552	Clinical (unspecified phase)
0.8542	High Similarity	NPD1550	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1549	Phase 2
0.8389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD4380	Phase 2
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8322	Intermediate Similarity	NPD1511	Approved
0.8264	Intermediate Similarity	NPD6651	Approved
0.8247	Intermediate Similarity	NPD1934	Approved
0.8219	Intermediate Similarity	NPD2796	Approved
0.8212	Intermediate Similarity	NPD1512	Approved
0.8194	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8176	Intermediate Similarity	NPD2800	Approved
0.8153	Intermediate Similarity	NPD7075	Discontinued
0.8121	Intermediate Similarity	NPD3750	Approved
0.8117	Intermediate Similarity	NPD6599	Discontinued
0.8095	Intermediate Similarity	NPD6100	Approved
0.8095	Intermediate Similarity	NPD6099	Approved
0.8095	Intermediate Similarity	NPD1551	Phase 2
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8089	Intermediate Similarity	NPD7768	Phase 2
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5711	Approved
0.8063	Intermediate Similarity	NPD5710	Approved
0.8054	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD3226	Approved
0.8038	Intermediate Similarity	NPD3749	Approved
0.8037	Intermediate Similarity	NPD5844	Phase 1
0.8029	Intermediate Similarity	NPD1651	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.7986	Intermediate Similarity	NPD1201	Approved
0.7973	Intermediate Similarity	NPD5408	Approved
0.7973	Intermediate Similarity	NPD5404	Approved
0.7973	Intermediate Similarity	NPD5405	Approved
0.7973	Intermediate Similarity	NPD5406	Approved
0.7961	Intermediate Similarity	NPD6799	Approved
0.7943	Intermediate Similarity	NPD1283	Approved
0.7919	Intermediate Similarity	NPD2346	Discontinued
0.7917	Intermediate Similarity	NPD4625	Phase 3
0.7898	Intermediate Similarity	NPD6801	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7887	Intermediate Similarity	NPD1470	Approved
0.7853	Intermediate Similarity	NPD6166	Phase 2
0.7853	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5494	Approved
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD920	Approved
0.78	Intermediate Similarity	NPD2344	Approved
0.7799	Intermediate Similarity	NPD3817	Phase 2
0.7785	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7003	Approved
0.774	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1465	Phase 2
0.773	Intermediate Similarity	NPD1281	Approved
0.7711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3972	Approved
0.7667	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7654	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5953	Discontinued
0.7605	Intermediate Similarity	NPD7054	Approved
0.7597	Intermediate Similarity	NPD2309	Approved
0.7595	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4626	Approved
0.7586	Intermediate Similarity	NPD2798	Approved
0.7586	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2654	Approved
0.7576	Intermediate Similarity	NPD3926	Phase 2
0.7564	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1247	Approved
0.756	Intermediate Similarity	NPD7472	Approved
0.7517	Intermediate Similarity	NPD1164	Approved
0.7517	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7471	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD230	Phase 1
0.7466	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD37	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1471	Phase 3
0.7431	Intermediate Similarity	NPD1608	Approved
0.7427	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD7229	Phase 3
0.74	Intermediate Similarity	NPD2979	Phase 3
0.7383	Intermediate Similarity	NPD411	Approved
0.7383	Intermediate Similarity	NPD2313	Discontinued
0.7379	Intermediate Similarity	NPD4749	Approved
0.7379	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7362	Intermediate Similarity	NPD5402	Approved
0.7361	Intermediate Similarity	NPD1610	Phase 2
0.7358	Intermediate Similarity	NPD5403	Approved
0.7351	Intermediate Similarity	NPD8151	Discontinued
0.7337	Intermediate Similarity	NPD7177	Discontinued
0.7333	Intermediate Similarity	NPD6234	Discontinued
0.7329	Intermediate Similarity	NPD1876	Approved
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4966	Approved
0.7317	Intermediate Similarity	NPD4967	Phase 2
0.7317	Intermediate Similarity	NPD4965	Approved
0.731	Intermediate Similarity	NPD9717	Approved
0.7305	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6781	Approved
0.7293	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6777	Approved
0.7293	Intermediate Similarity	NPD6782	Approved
0.7293	Intermediate Similarity	NPD6776	Approved
0.7293	Intermediate Similarity	NPD6778	Approved
0.7293	Intermediate Similarity	NPD6779	Approved
0.7293	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7283	Intermediate Similarity	NPD8312	Approved
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7273	Intermediate Similarity	NPD5691	Approved
0.7267	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6832	Phase 2
0.7241	Intermediate Similarity	NPD422	Phase 1
0.7241	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD17	Approved
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7207	Intermediate Similarity	NPD4363	Phase 3
0.7207	Intermediate Similarity	NPD4360	Phase 2
0.7203	Intermediate Similarity	NPD9545	Approved
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.72	Intermediate Similarity	NPD3027	Phase 3
0.7181	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7697	Approved
0.7174	Intermediate Similarity	NPD7435	Discontinued
0.7174	Intermediate Similarity	NPD7698	Approved
0.7174	Intermediate Similarity	NPD7696	Phase 3
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.717	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4361	Phase 2
0.7162	Intermediate Similarity	NPD2797	Approved
0.7161	Intermediate Similarity	NPD2531	Phase 2
0.7159	Intermediate Similarity	NPD8150	Discontinued
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4288	Approved
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD447	Suspended
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7081	Intermediate Similarity	NPD6273	Approved
0.7079	Intermediate Similarity	NPD4287	Approved
0.7069	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD9494	Approved
0.7059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1613	Approved
0.7059	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4477	Approved
0.7051	Intermediate Similarity	NPD4476	Approved
0.705	Intermediate Similarity	NPD4750	Phase 3

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