NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.05
Volume:	235.867
LogP:	3.243
LogD:	2.667
LogS:	-3.236
# Rotatable Bonds:	1
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	2.924
Fsp3:	0.077
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:	-4.977
MDCK Permeability:	6.077497346268501e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	95.85133361816406%
Volume Distribution (VD):	0.564
Pgp-substrate:	7.9067864418029785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.532
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	11.562
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.699
Maximum Recommended Daily Dose:	0.682
Skin Sensitization:	0.918
Carcinogencity:	0.673
Eye Corrosion:	0.006
Eye Irritation:	0.891
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC119929

Natural Product ID:	NPC119929
*Common Name:**	6-Methoxysorigenin
IUPAC Name:	8,9-dihydroxy-6-methoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:	6-Methoxysorigenin
Standard InCHIKey:	HOHPIALGJUPOAZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10O5/c1-17-8-3-6-2-7-5-18-13(16)11(7)12(15)10(6)9(14)4-8/h2-4,14-15H,5H2,1H3
SMILES:	COc1cc(O)c2c(c1)cc1c(c2O)C(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455630
PubChem CID:	12442904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO23980	Rhamnus nakaharai	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691213]
NPO23980	Rhamnus nakaharai	Species	Rhamnaceae	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
Others	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	88.1	%	PMID[496311]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.1	%	PMID[496311]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	41.7	%	PMID[496311]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	80.0	%	PMID[496311]

☑ 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 NPC119929 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	369
0.1-0.2	1747
0.2-0.3	3751
0.3-0.4	8518
0.4-0.5	9818
0.5-0.6	3600
0.6-0.7	5612
0.7-0.8	6053
0.8-0.85	2602
0.85-0.9	538
0.9-0.95	88
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC271681
0.9459	High Similarity	NPC175978
0.9379	High Similarity	NPC75694
0.9371	High Similarity	NPC90411
0.9329	High Similarity	NPC273483
0.9315	High Similarity	NPC163846
0.9315	High Similarity	NPC225173
0.9306	High Similarity	NPC182255
0.9306	High Similarity	NPC94076
0.9301	High Similarity	NPC165172
0.9257	High Similarity	NPC291049
0.9257	High Similarity	NPC233267
0.9252	High Similarity	NPC8817
0.9252	High Similarity	NPC125801
0.9252	High Similarity	NPC137296
0.9241	High Similarity	NPC84266
0.9231	High Similarity	NPC275356
0.92	High Similarity	NPC217447
0.9195	High Similarity	NPC202595
0.9189	High Similarity	NPC2569
0.9189	High Similarity	NPC172329
0.9189	High Similarity	NPC105415
0.9184	High Similarity	NPC470357
0.9145	High Similarity	NPC146211
0.9145	High Similarity	NPC180924
0.9133	High Similarity	NPC133856
0.9122	High Similarity	NPC166583
0.9122	High Similarity	NPC7943
0.9122	High Similarity	NPC53362
0.9122	High Similarity	NPC22005
0.9122	High Similarity	NPC123202
0.9091	High Similarity	NPC135837
0.9091	High Similarity	NPC143050
0.9085	High Similarity	NPC263483
0.9085	High Similarity	NPC164110
0.9085	High Similarity	NPC212967
0.9085	High Similarity	NPC96342
0.9085	High Similarity	NPC246647
0.9079	High Similarity	NPC149618
0.9079	High Similarity	NPC89625
0.9067	High Similarity	NPC325983
0.9067	High Similarity	NPC147735
0.9067	High Similarity	NPC179178
0.906	High Similarity	NPC7025
0.906	High Similarity	NPC256672
0.906	High Similarity	NPC27221
0.9054	High Similarity	NPC260946
0.9054	High Similarity	NPC267509
0.9048	High Similarity	NPC470932
0.9048	High Similarity	NPC471305
0.9041	High Similarity	NPC250755
0.9021	High Similarity	NPC158481
0.9007	High Similarity	NPC149526
0.9007	High Similarity	NPC232645
0.9007	High Similarity	NPC72958
0.9007	High Similarity	NPC204350
0.9007	High Similarity	NPC474417
0.9	High Similarity	NPC158338
0.9	High Similarity	NPC288036
0.9	High Similarity	NPC97029
0.9	High Similarity	NPC100985
0.9	High Similarity	NPC97028
0.9	High Similarity	NPC198927
0.9	High Similarity	NPC65589
0.8994	High Similarity	NPC477571
0.8994	High Similarity	NPC477573
0.8994	High Similarity	NPC477572
0.8993	High Similarity	NPC56433
0.8993	High Similarity	NPC126767
0.8993	High Similarity	NPC118027
0.8993	High Similarity	NPC289042
0.8993	High Similarity	NPC245584
0.8993	High Similarity	NPC34802
0.8993	High Similarity	NPC190648
0.8993	High Similarity	NPC312929
0.8986	High Similarity	NPC473692
0.8986	High Similarity	NPC134621
0.8986	High Similarity	NPC32470
0.898	High Similarity	NPC159721
0.898	High Similarity	NPC51106
0.898	High Similarity	NPC472006
0.898	High Similarity	NPC469542
0.8973	High Similarity	NPC37530
0.8973	High Similarity	NPC67650
0.8973	High Similarity	NPC1704
0.8973	High Similarity	NPC220106
0.8968	High Similarity	NPC470810
0.8968	High Similarity	NPC47623
0.8954	High Similarity	NPC148938
0.8951	High Similarity	NPC182496
0.8951	High Similarity	NPC180905
0.8947	High Similarity	NPC87708
0.8947	High Similarity	NPC40356
0.8947	High Similarity	NPC154683
0.894	High Similarity	NPC255641
0.894	High Similarity	NPC470107
0.894	High Similarity	NPC290954
0.894	High Similarity	NPC470568
0.894	High Similarity	NPC294646
0.8933	High Similarity	NPC37139
0.8926	High Similarity	NPC237208
0.8926	High Similarity	NPC138978
0.8926	High Similarity	NPC107625
0.8926	High Similarity	NPC473927
0.8919	High Similarity	NPC95123
0.8919	High Similarity	NPC42540
0.8919	High Similarity	NPC151607
0.8919	High Similarity	NPC19896
0.8919	High Similarity	NPC66404
0.8912	High Similarity	NPC105648
0.891	High Similarity	NPC117985
0.8904	High Similarity	NPC168471
0.8904	High Similarity	NPC99441
0.8903	High Similarity	NPC45846
0.8889	High Similarity	NPC472799
0.8889	High Similarity	NPC169990
0.8889	High Similarity	NPC235333
0.8889	High Similarity	NPC50455
0.8889	High Similarity	NPC210942
0.8882	High Similarity	NPC115324
0.8882	High Similarity	NPC470569
0.8882	High Similarity	NPC240768
0.8882	High Similarity	NPC258249
0.8882	High Similarity	NPC200773
0.8882	High Similarity	NPC58668
0.8882	High Similarity	NPC106372
0.8882	High Similarity	NPC478148
0.8875	High Similarity	NPC17219
0.8874	High Similarity	NPC70764
0.8874	High Similarity	NPC329933
0.8868	High Similarity	NPC473094
0.8867	High Similarity	NPC71055
0.8859	High Similarity	NPC29577
0.8854	High Similarity	NPC144843
0.8851	High Similarity	NPC471731
0.8844	High Similarity	NPC149533
0.8836	High Similarity	NPC88269
0.8831	High Similarity	NPC199926
0.8831	High Similarity	NPC213936
0.8831	High Similarity	NPC297531
0.8824	High Similarity	NPC207624
0.8816	High Similarity	NPC295036
0.8816	High Similarity	NPC96501
0.8816	High Similarity	NPC158866
0.8816	High Similarity	NPC150928
0.8812	High Similarity	NPC473095
0.8812	High Similarity	NPC473096
0.8811	High Similarity	NPC153783
0.8808	High Similarity	NPC216624
0.8808	High Similarity	NPC153417
0.8808	High Similarity	NPC470359
0.8808	High Similarity	NPC5537
0.8805	High Similarity	NPC477835
0.8797	High Similarity	NPC156082
0.879	High Similarity	NPC24761
0.8784	High Similarity	NPC18714
0.8784	High Similarity	NPC49108
0.8784	High Similarity	NPC469579
0.8784	High Similarity	NPC322112
0.8784	High Similarity	NPC82913
0.8784	High Similarity	NPC471733
0.8784	High Similarity	NPC297985
0.8784	High Similarity	NPC474385
0.8782	High Similarity	NPC474373
0.8782	High Similarity	NPC470339
0.8782	High Similarity	NPC324736
0.8776	High Similarity	NPC472601
0.8776	High Similarity	NPC155205
0.8776	High Similarity	NPC472600
0.8774	High Similarity	NPC150227
0.8773	High Similarity	NPC324220
0.8773	High Similarity	NPC312630
0.8766	High Similarity	NPC183874
0.8766	High Similarity	NPC477669
0.8766	High Similarity	NPC208806
0.8766	High Similarity	NPC135522
0.8766	High Similarity	NPC477691
0.8766	High Similarity	NPC329844
0.8766	High Similarity	NPC192189
0.8759	High Similarity	NPC235115
0.8758	High Similarity	NPC170169
0.8758	High Similarity	NPC193976
0.8758	High Similarity	NPC23668
0.8758	High Similarity	NPC230848
0.8758	High Similarity	NPC227166
0.8758	High Similarity	NPC39819
0.8758	High Similarity	NPC70016
0.8758	High Similarity	NPC215921
0.875	High Similarity	NPC270160
0.875	High Similarity	NPC77325
0.875	High Similarity	NPC476684
0.875	High Similarity	NPC175943
0.875	High Similarity	NPC178202
0.875	High Similarity	NPC237440
0.875	High Similarity	NPC4423
0.8742	High Similarity	NPC17816
0.8742	High Similarity	NPC112981
0.8733	High Similarity	NPC28632
0.8733	High Similarity	NPC131766
0.8726	High Similarity	NPC472055

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 NPC119929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	991
0.2-0.3	1659
0.3-0.4	2559
0.4-0.5	1862
0.5-0.6	1135
0.6-0.7	386
0.7-0.8	170
0.8-0.85	32
0.85-0.9	8
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9379	High Similarity	NPD2533	Approved
0.9379	High Similarity	NPD2534	Approved
0.9379	High Similarity	NPD2532	Approved
0.8966	High Similarity	NPD970	Clinical (unspecified phase)
0.8854	High Similarity	NPD6232	Discontinued
0.8688	High Similarity	NPD7473	Discontinued
0.8645	High Similarity	NPD7819	Suspended
0.8616	High Similarity	NPD5711	Approved
0.8616	High Similarity	NPD5710	Approved
0.8553	High Similarity	NPD6959	Discontinued
0.8493	Intermediate Similarity	NPD1607	Approved
0.8378	Intermediate Similarity	NPD1510	Phase 2
0.8378	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD920	Approved
0.8366	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD3749	Approved
0.8356	Intermediate Similarity	NPD1240	Approved
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8322	Intermediate Similarity	NPD1551	Phase 2
0.8291	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1243	Approved
0.8278	Intermediate Similarity	NPD2800	Approved
0.8269	Intermediate Similarity	NPD3226	Approved
0.8267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8212	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD7768	Phase 2
0.8165	Intermediate Similarity	NPD7411	Suspended
0.8146	Intermediate Similarity	NPD2346	Discontinued
0.8137	Intermediate Similarity	NPD7075	Discontinued
0.8117	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1934	Approved
0.8105	Intermediate Similarity	NPD3750	Approved
0.8101	Intermediate Similarity	NPD4380	Phase 2
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8095	Intermediate Similarity	NPD6559	Discontinued
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8065	Intermediate Similarity	NPD7390	Discontinued
0.8065	Intermediate Similarity	NPD1511	Approved
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD919	Approved
0.7963	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD2801	Approved
0.7949	Intermediate Similarity	NPD6799	Approved
0.7939	Intermediate Similarity	NPD7229	Phase 3
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7931	Intermediate Similarity	NPD1283	Approved
0.7927	Intermediate Similarity	NPD5494	Approved
0.7901	Intermediate Similarity	NPD3817	Phase 2
0.7898	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6801	Discontinued
0.7888	Intermediate Similarity	NPD37	Approved
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7853	Intermediate Similarity	NPD4967	Phase 2
0.7853	Intermediate Similarity	NPD4966	Approved
0.7853	Intermediate Similarity	NPD4965	Approved
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD5406	Approved
0.7843	Intermediate Similarity	NPD5404	Approved
0.7843	Intermediate Similarity	NPD5405	Approved
0.7843	Intermediate Similarity	NPD2796	Approved
0.7843	Intermediate Similarity	NPD5408	Approved
0.7806	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2344	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD1247	Approved
0.7756	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD3764	Approved
0.7733	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1281	Approved
0.7719	Intermediate Similarity	NPD5953	Discontinued
0.7706	Intermediate Similarity	NPD7286	Phase 2
0.7702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6651	Approved
0.7643	Intermediate Similarity	NPD7003	Approved
0.7635	Intermediate Similarity	NPD1203	Approved
0.7633	Intermediate Similarity	NPD6166	Phase 2
0.7633	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2979	Phase 3
0.7632	Intermediate Similarity	NPD943	Approved
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7613	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD6099	Approved
0.7602	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2309	Approved
0.7576	Intermediate Similarity	NPD5402	Approved
0.7564	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7074	Phase 3
0.7551	Intermediate Similarity	NPD1608	Approved
0.755	Intermediate Similarity	NPD4625	Phase 3
0.7544	Intermediate Similarity	NPD7228	Approved
0.754	Intermediate Similarity	NPD8151	Discontinued
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1470	Approved
0.7517	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD7054	Approved
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7483	Intermediate Similarity	NPD1201	Approved
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD447	Suspended
0.7466	Intermediate Similarity	NPD4626	Approved
0.7457	Intermediate Similarity	NPD7472	Approved
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7453	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1471	Phase 3
0.7448	Intermediate Similarity	NPD9545	Approved
0.7442	Intermediate Similarity	NPD7177	Discontinued
0.7442	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9717	Approved
0.7414	Intermediate Similarity	NPD6797	Phase 2
0.7414	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1651	Approved
0.7397	Intermediate Similarity	NPD5691	Approved
0.7391	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2438	Suspended
0.7378	Intermediate Similarity	NPD7458	Discontinued
0.7374	Intermediate Similarity	NPD4287	Approved
0.7371	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7365	Intermediate Similarity	NPD422	Phase 1
0.7362	Intermediate Similarity	NPD5403	Approved
0.736	Intermediate Similarity	NPD8150	Discontinued
0.7347	Intermediate Similarity	NPD17	Approved
0.7346	Intermediate Similarity	NPD5401	Approved
0.733	Intermediate Similarity	NPD7808	Phase 3
0.7325	Intermediate Similarity	NPD4308	Phase 3
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD9493	Approved
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6273	Approved
0.7297	Intermediate Similarity	NPD6776	Approved
0.7297	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD6777	Approved
0.7297	Intermediate Similarity	NPD6782	Approved
0.7297	Intermediate Similarity	NPD6779	Approved
0.7297	Intermediate Similarity	NPD6778	Approved
0.7297	Intermediate Similarity	NPD6780	Approved
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2531	Phase 2
0.7277	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD4288	Approved
0.725	Intermediate Similarity	NPD2654	Approved
0.7248	Intermediate Similarity	NPD1611	Approved
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD9269	Phase 2
0.7193	Intermediate Similarity	NPD6746	Phase 2
0.7181	Intermediate Similarity	NPD7698	Approved
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7175	Intermediate Similarity	NPD7240	Approved
0.7171	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD4476	Approved
0.717	Intermediate Similarity	NPD4477	Approved
0.7168	Intermediate Similarity	NPD5242	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7874	Approved
0.7125	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6004	Phase 3
0.7125	Intermediate Similarity	NPD6002	Phase 3
0.7125	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6005	Phase 3
0.7124	Intermediate Similarity	NPD2798	Approved
0.7124	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1019	Discontinued
0.7114	Intermediate Similarity	NPD1778	Approved
0.7112	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3787	Discontinued

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