NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	267.823
LogP:	2.778
LogD:	2.513
LogS:	-3.344
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	2.859
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.883
MDCK Permeability:	7.924842066131532e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.275
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	96.32317352294922%
Volume Distribution (VD):	0.567
Pgp-substrate:	2.97236967086792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.699
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.839
CYP2D6-substrate:	0.69
CYP3A4-inhibitor:	0.812
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	16.105
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.656
AMES Toxicity:	0.271
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.328
Skin Sensitization:	0.928
Carcinogencity:	0.622
Eye Corrosion:	0.01
Eye Irritation:	0.942
Respiratory Toxicity:	0.115

Download Data

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

Natural Product: NPC155205

Natural Product ID:	NPC155205
*Common Name:**	Thunberginol C
IUPAC Name:	6,8-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydroisochromen-1-one
Synonyms:	thunberginol C
Standard InCHIKey:	WMAITHDYVBQITD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O5/c16-10-3-1-8(2-4-10)13-6-9-5-11(17)7-12(18)14(9)15(19)20-13/h1-5,7,13,16-18H,6H2
SMILES:	Oc1ccc(cc1)C1OC(=O)c2c(C1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL69267
PubChem CID:	10333412
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid 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
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11549443]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17609121]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9871657]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24728	Tragopogon porrifolius	Species	Asteraceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-9.3	%	PMID[549742]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-11.1	%	PMID[549742]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-17.6	%	PMID[549742]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	1.4	%	PMID[549742]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-7.5	%	PMID[549742]

☑ 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 NPC155205 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	360
0.1-0.2	1582
0.2-0.3	3562
0.3-0.4	7973
0.4-0.5	10431
0.5-0.6	3743
0.6-0.7	6121
0.7-0.8	6689
0.8-0.85	1747
0.85-0.9	433
0.9-0.95	51
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9774	High Similarity	NPC261292
0.9774	High Similarity	NPC301915
0.9556	High Similarity	NPC472602
0.9552	High Similarity	NPC235115
0.95	High Similarity	NPC476463
0.9489	High Similarity	NPC53649
0.9343	High Similarity	NPC88269
0.9338	High Similarity	NPC70380
0.9328	High Similarity	NPC153783
0.9286	High Similarity	NPC151607
0.9286	High Similarity	NPC42540
0.9275	High Similarity	NPC472600
0.9275	High Similarity	NPC472601
0.927	High Similarity	NPC191835
0.927	High Similarity	NPC212693
0.927	High Similarity	NPC94248
0.927	High Similarity	NPC478200
0.927	High Similarity	NPC33144
0.9265	High Similarity	NPC291454
0.9214	High Similarity	NPC478202
0.9214	High Similarity	NPC159721
0.9214	High Similarity	NPC469542
0.9209	High Similarity	NPC472603
0.9209	High Similarity	NPC472604
0.9209	High Similarity	NPC313123
0.9209	High Similarity	NPC478217
0.9209	High Similarity	NPC472605
0.9209	High Similarity	NPC158634
0.9203	High Similarity	NPC105456
0.9203	High Similarity	NPC139634
0.9203	High Similarity	NPC268052
0.9203	High Similarity	NPC32360
0.9197	High Similarity	NPC71256
0.9191	High Similarity	NPC142027
0.9191	High Similarity	NPC27407
0.9179	High Similarity	NPC470831
0.9179	High Similarity	NPC219892
0.9179	High Similarity	NPC189823
0.9179	High Similarity	NPC214702
0.9161	High Similarity	NPC221352
0.9155	High Similarity	NPC267509
0.9143	High Similarity	NPC250755
0.9143	High Similarity	NPC471733
0.9137	High Similarity	NPC158472
0.913	High Similarity	NPC221104
0.9118	High Similarity	NPC175943
0.9085	High Similarity	NPC32470
0.9078	High Similarity	NPC472610
0.9078	High Similarity	NPC471731
0.9071	High Similarity	NPC472035
0.9071	High Similarity	NPC1704
0.9071	High Similarity	NPC470842
0.9071	High Similarity	NPC67650
0.9071	High Similarity	NPC478201
0.9065	High Similarity	NPC52358
0.9065	High Similarity	NPC247409
0.9058	High Similarity	NPC135837
0.9034	High Similarity	NPC470107
0.9021	High Similarity	NPC51513
0.9021	High Similarity	NPC202112
0.9021	High Similarity	NPC473023
0.9014	High Similarity	NPC257025
0.9007	High Similarity	NPC474385
0.9007	High Similarity	NPC469579
0.8986	High Similarity	NPC50455
0.8986	High Similarity	NPC227062
0.8986	High Similarity	NPC158481
0.8971	High Similarity	NPC476389
0.8966	High Similarity	NPC4423
0.8966	High Similarity	NPC77325
0.8966	High Similarity	NPC476684
0.8966	High Similarity	NPC270160
0.8966	High Similarity	NPC237440
0.8958	High Similarity	NPC81835
0.8951	High Similarity	NPC134621
0.8951	High Similarity	NPC83272
0.8944	High Similarity	NPC51106
0.8944	High Similarity	NPC472006
0.8944	High Similarity	NPC310340
0.8936	High Similarity	NPC244923
0.8936	High Similarity	NPC475730
0.8936	High Similarity	NPC275734
0.8936	High Similarity	NPC37530
0.8936	High Similarity	NPC220106
0.8936	High Similarity	NPC182421
0.8929	High Similarity	NPC275356
0.8929	High Similarity	NPC92655
0.8921	High Similarity	NPC474771
0.8921	High Similarity	NPC474849
0.8921	High Similarity	NPC65837
0.8921	High Similarity	NPC149372
0.8921	High Similarity	NPC194579
0.8921	High Similarity	NPC178467
0.8913	High Similarity	NPC182496
0.8913	High Similarity	NPC180905
0.8912	High Similarity	NPC167903
0.8897	High Similarity	NPC106328
0.8897	High Similarity	NPC35150
0.8889	High Similarity	NPC225173
0.8889	High Similarity	NPC163846
0.8889	High Similarity	NPC237208
0.8889	High Similarity	NPC471735
0.8881	High Similarity	NPC280404
0.8881	High Similarity	NPC126882
0.8881	High Similarity	NPC478203
0.8881	High Similarity	NPC66404
0.8881	High Similarity	NPC210425
0.8881	High Similarity	NPC86373
0.8881	High Similarity	NPC277426
0.8881	High Similarity	NPC210966
0.8881	High Similarity	NPC95123
0.8873	High Similarity	NPC82913
0.8873	High Similarity	NPC105648
0.8865	High Similarity	NPC316480
0.8865	High Similarity	NPC99441
0.8857	High Similarity	NPC296490
0.8857	High Similarity	NPC9121
0.8857	High Similarity	NPC287246
0.8857	High Similarity	NPC197666
0.8857	High Similarity	NPC79943
0.8857	High Similarity	NPC212767
0.8857	High Similarity	NPC32441
0.8857	High Similarity	NPC12296
0.8857	High Similarity	NPC475974
0.8857	High Similarity	NPC243083
0.8857	High Similarity	NPC295261
0.8857	High Similarity	NPC126739
0.8857	High Similarity	NPC107586
0.8857	High Similarity	NPC13768
0.8857	High Similarity	NPC177307
0.8844	High Similarity	NPC215921
0.8844	High Similarity	NPC70016
0.8844	High Similarity	NPC227166
0.8828	High Similarity	NPC471734
0.8828	High Similarity	NPC125801
0.8819	High Similarity	NPC472034
0.8819	High Similarity	NPC257558
0.8819	High Similarity	NPC473692
0.8819	High Similarity	NPC29577
0.8819	High Similarity	NPC131766
0.8811	High Similarity	NPC73028
0.8803	High Similarity	NPC90411
0.8794	High Similarity	NPC474655
0.8794	High Similarity	NPC472460
0.8794	High Similarity	NPC329225
0.8794	High Similarity	NPC147686
0.8786	High Similarity	NPC245058
0.8786	High Similarity	NPC193792
0.8784	High Similarity	NPC295646
0.8784	High Similarity	NPC474843
0.8776	High Similarity	NPC475460
0.8776	High Similarity	NPC194379
0.8776	High Similarity	NPC119929
0.8776	High Similarity	NPC472891
0.8776	High Similarity	NPC295036
0.8759	High Similarity	NPC470570
0.8759	High Similarity	NPC107625
0.8759	High Similarity	NPC472033
0.8759	High Similarity	NPC138978
0.875	High Similarity	NPC48762
0.875	High Similarity	NPC470932
0.875	High Similarity	NPC21599
0.875	High Similarity	NPC193703
0.8741	High Similarity	NPC49108
0.8741	High Similarity	NPC322112
0.8732	High Similarity	NPC20709
0.8732	High Similarity	NPC222342
0.8732	High Similarity	NPC168471
0.8732	High Similarity	NPC225153
0.8732	High Similarity	NPC150648
0.8732	High Similarity	NPC310135
0.8732	High Similarity	NPC165172
0.8732	High Similarity	NPC254994
0.8732	High Similarity	NPC274784
0.8732	High Similarity	NPC265871
0.8732	High Similarity	NPC329203
0.8731	High Similarity	NPC262671
0.8731	High Similarity	NPC201728
0.8725	High Similarity	NPC125487
0.8725	High Similarity	NPC281703
0.8723	High Similarity	NPC476480
0.8723	High Similarity	NPC472403
0.8723	High Similarity	NPC84585
0.8716	High Similarity	NPC204561
0.8716	High Similarity	NPC204350
0.8716	High Similarity	NPC317715
0.8716	High Similarity	NPC316960
0.8716	High Similarity	NPC148945
0.8716	High Similarity	NPC309512
0.8716	High Similarity	NPC72958
0.8716	High Similarity	NPC232645
0.8716	High Similarity	NPC78835
0.8714	High Similarity	NPC39426
0.8714	High Similarity	NPC234560
0.8714	High Similarity	NPC118919
0.8714	High Similarity	NPC156967
0.8714	High Similarity	NPC472599
0.8707	High Similarity	NPC233267
0.8707	High Similarity	NPC84142
0.8707	High Similarity	NPC291049

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 NPC155205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	900
0.2-0.3	1566
0.3-0.4	2610
0.4-0.5	1922
0.5-0.6	1208
0.6-0.7	418
0.7-0.8	140
0.8-0.85	32
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD970	Clinical (unspecified phase)
0.8857	High Similarity	NPD1550	Clinical (unspecified phase)
0.8857	High Similarity	NPD1552	Clinical (unspecified phase)
0.8794	High Similarity	NPD1549	Phase 2
0.8725	High Similarity	NPD7819	Suspended
0.8714	High Similarity	NPD1510	Phase 2
0.8429	Intermediate Similarity	NPD1240	Approved
0.8414	Intermediate Similarity	NPD3750	Approved
0.8411	Intermediate Similarity	NPD1934	Approved
0.8355	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7075	Discontinued
0.8312	Intermediate Similarity	NPD3749	Approved
0.8311	Intermediate Similarity	NPD2533	Approved
0.8311	Intermediate Similarity	NPD2534	Approved
0.8311	Intermediate Similarity	NPD2532	Approved
0.831	Intermediate Similarity	NPD1607	Approved
0.8278	Intermediate Similarity	NPD4380	Phase 2
0.8264	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7411	Suspended
0.8217	Intermediate Similarity	NPD6232	Discontinued
0.8188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD943	Approved
0.8156	Intermediate Similarity	NPD3764	Approved
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8138	Intermediate Similarity	NPD2796	Approved
0.8133	Intermediate Similarity	NPD1512	Approved
0.8129	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD230	Phase 1
0.8077	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD3748	Approved
0.8063	Intermediate Similarity	NPD7473	Discontinued
0.8029	Intermediate Similarity	NPD1201	Approved
0.8014	Intermediate Similarity	NPD5408	Approved
0.8014	Intermediate Similarity	NPD5405	Approved
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8014	Intermediate Similarity	NPD5404	Approved
0.8014	Intermediate Similarity	NPD5406	Approved
0.8013	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD9545	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7935	Intermediate Similarity	NPD6801	Discontinued
0.7929	Intermediate Similarity	NPD1470	Approved
0.7922	Intermediate Similarity	NPD6599	Discontinued
0.7902	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6166	Phase 2
0.7885	Intermediate Similarity	NPD2801	Approved
0.7881	Intermediate Similarity	NPD7390	Discontinued
0.7852	Intermediate Similarity	NPD9493	Approved
0.7829	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7074	Phase 3
0.7801	Intermediate Similarity	NPD1164	Approved
0.7801	Intermediate Similarity	NPD1203	Approved
0.78	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7785	Intermediate Similarity	NPD3882	Suspended
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5711	Approved
0.7764	Intermediate Similarity	NPD5710	Approved
0.7744	Intermediate Similarity	NPD7054	Approved
0.7742	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5403	Approved
0.7722	Intermediate Similarity	NPD5402	Approved
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7712	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7472	Approved
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD1610	Phase 2
0.764	Intermediate Similarity	NPD5494	Approved
0.7636	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1243	Approved
0.7613	Intermediate Similarity	NPD920	Approved
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.7605	Intermediate Similarity	NPD6559	Discontinued
0.7597	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7808	Phase 3
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6190	Approved
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD8150	Discontinued
0.7469	Intermediate Similarity	NPD919	Approved
0.7467	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7465	Intermediate Similarity	NPD9269	Phase 2
0.7465	Intermediate Similarity	NPD9717	Approved
0.7464	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5953	Discontinued
0.7432	Intermediate Similarity	NPD1613	Approved
0.7432	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD9268	Approved
0.7415	Intermediate Similarity	NPD2313	Discontinued
0.7397	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD6832	Phase 2
0.7394	Intermediate Similarity	NPD422	Phase 1
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD74	Approved
0.7388	Intermediate Similarity	NPD9266	Approved
0.7383	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7199	Phase 2
0.7376	Intermediate Similarity	NPD17	Approved
0.7375	Intermediate Similarity	NPD37	Approved
0.7368	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7362	Intermediate Similarity	NPD6234	Discontinued
0.7361	Intermediate Similarity	NPD1283	Approved
0.7357	Intermediate Similarity	NPD1548	Phase 1
0.7346	Intermediate Similarity	NPD4967	Phase 2
0.7346	Intermediate Similarity	NPD4966	Approved
0.7346	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD6651	Approved
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.7321	Intermediate Similarity	NPD7286	Phase 2
0.7313	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD9263	Approved
0.7313	Intermediate Similarity	NPD9264	Approved
0.7313	Intermediate Similarity	NPD9267	Approved
0.731	Intermediate Similarity	NPD8313	Approved
0.731	Intermediate Similarity	NPD8312	Approved
0.731	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4287	Approved
0.7297	Intermediate Similarity	NPD3268	Approved
0.7297	Intermediate Similarity	NPD411	Approved
0.7297	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD447	Suspended
0.726	Intermediate Similarity	NPD2798	Approved
0.7251	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD520	Approved
0.7241	Intermediate Similarity	NPD3225	Approved
0.7237	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7229	Intermediate Similarity	NPD3787	Discontinued
0.7226	Intermediate Similarity	NPD7003	Approved
0.7215	Intermediate Similarity	NPD6273	Approved
0.7211	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1296	Phase 2
0.7179	Intermediate Similarity	NPD2309	Approved
0.7171	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7228	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD6534	Approved
0.7133	Intermediate Similarity	NPD6663	Approved
0.7104	Intermediate Similarity	NPD7435	Discontinued
0.7097	Intermediate Similarity	NPD8151	Discontinued
0.7095	Intermediate Similarity	NPD2861	Phase 2
0.7095	Intermediate Similarity	NPD5736	Approved
0.7086	Intermediate Similarity	NPD4060	Phase 1
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3266	Approved
0.7075	Intermediate Similarity	NPD3267	Approved
0.7071	Intermediate Similarity	NPD9281	Approved
0.7067	Intermediate Similarity	NPD6798	Discontinued
0.7066	Intermediate Similarity	NPD1247	Approved
0.7065	Intermediate Similarity	NPD8320	Phase 1
0.7065	Intermediate Similarity	NPD8319	Approved
0.7059	Intermediate Similarity	NPD7177	Discontinued
0.7039	Intermediate Similarity	NPD4360	Phase 2
0.7039	Intermediate Similarity	NPD4363	Phase 3
0.7039	Intermediate Similarity	NPD6355	Discontinued
0.7033	Intermediate Similarity	NPD6780	Approved
0.7033	Intermediate Similarity	NPD6777	Approved
0.7033	Intermediate Similarity	NPD6779	Approved
0.7033	Intermediate Similarity	NPD6781	Approved
0.7033	Intermediate Similarity	NPD6778	Approved
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6782	Approved
0.7033	Intermediate Similarity	NPD6776	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