NPASS Compound

Structure

NPC474095 OpenBabel07101718222D 21 23 0 0 1 0 0 0 0 0999 V2000 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.14
Volume:	304.767
LogP:	3.897
LogD:	3.149
LogS:	-5.387
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	3.849
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.964
MDCK Permeability:	1.9382328900974244e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	96.78414916992188%
Volume Distribution (VD):	2.5
Pgp-substrate:	3.010319948196411%

ADMET: Metabolism

CYP1A2-inhibitor:	0.863
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.737
CYP2C19-substrate:	0.749
CYP2C9-inhibitor:	0.623
CYP2C9-substrate:	0.395
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.439
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	1.552
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.404
Drug-inuced Liver Injury (DILI):	0.632
AMES Toxicity:	0.747
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.808
Carcinogencity:	0.895
Eye Corrosion:	0.005
Eye Irritation:	0.831
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC474095

Natural Product ID:	NPC474095
*Common Name:**	Populene C
IUPAC Name:	1,4,4,6,9-pentamethyl-1,2-dihydrobenzo[f]isochromene-7,8-dione
Synonyms:	Populene C
Standard InCHIKey:	LKKQCDCZGYUJTA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H20O3/c1-9-7-13-14(11(3)8-21-18(13,4)5)12-6-10(2)16(19)17(20)15(9)12/h6-7,11H,8H2,1-5H3
SMILES:	CC1COC(C2=C1C3=C(C(=C2)C)C(=O)C(=O)C(=C3)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461300
PubChem CID:	24970696
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18553924]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19367	Thespesia populnea	Species	Malvaceae	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	4
MIC	2

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.35	ug.mL-1	PMID[468878]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3.4	ug.mL-1	PMID[468878]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2.9	ug.mL-1	PMID[468878]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[468878]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.69	ug.mL-1	PMID[468878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10.0	ug.mL-1	PMID[468878]

☑ 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 NPC474095 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	284
0.1-0.2	1392
0.2-0.3	2781
0.3-0.4	8032
0.4-0.5	12511
0.5-0.6	10541
0.6-0.7	6396
0.7-0.8	680
0.8-0.85	60
0.85-0.9	16
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC135730
0.8957	High Similarity	NPC232958
0.8929	High Similarity	NPC228936
0.8879	High Similarity	NPC144547
0.8793	High Similarity	NPC289432
0.8793	High Similarity	NPC238861
0.8793	High Similarity	NPC988
0.8793	High Similarity	NPC77000
0.875	High Similarity	NPC13784
0.8739	High Similarity	NPC210089
0.8571	High Similarity	NPC474057
0.8509	High Similarity	NPC196075
0.85	High Similarity	NPC51079
0.8496	Intermediate Similarity	NPC212415
0.8421	Intermediate Similarity	NPC128368
0.8348	Intermediate Similarity	NPC477411
0.8333	Intermediate Similarity	NPC79496
0.8273	Intermediate Similarity	NPC247976
0.825	Intermediate Similarity	NPC472981
0.8246	Intermediate Similarity	NPC167504
0.822	Intermediate Similarity	NPC45794
0.822	Intermediate Similarity	NPC228318
0.8205	Intermediate Similarity	NPC226093
0.819	Intermediate Similarity	NPC307651
0.8174	Intermediate Similarity	NPC82899
0.8174	Intermediate Similarity	NPC270699
0.8158	Intermediate Similarity	NPC196246
0.8158	Intermediate Similarity	NPC214067
0.813	Intermediate Similarity	NPC295664
0.812	Intermediate Similarity	NPC221275
0.812	Intermediate Similarity	NPC210092
0.8108	Intermediate Similarity	NPC301943
0.8108	Intermediate Similarity	NPC474365
0.8099	Intermediate Similarity	NPC50872
0.8091	Intermediate Similarity	NPC70624
0.8087	Intermediate Similarity	NPC305912
0.8087	Intermediate Similarity	NPC291799
0.8087	Intermediate Similarity	NPC1082
0.8087	Intermediate Similarity	NPC474157
0.808	Intermediate Similarity	NPC51448
0.808	Intermediate Similarity	NPC115797
0.807	Intermediate Similarity	NPC17417
0.807	Intermediate Similarity	NPC83628
0.807	Intermediate Similarity	NPC10251
0.807	Intermediate Similarity	NPC265407
0.8065	Intermediate Similarity	NPC470765
0.8053	Intermediate Similarity	NPC100767
0.8049	Intermediate Similarity	NPC85511
0.8049	Intermediate Similarity	NPC228739
0.8034	Intermediate Similarity	NPC326664
0.8034	Intermediate Similarity	NPC196673
0.8017	Intermediate Similarity	NPC292834
0.8017	Intermediate Similarity	NPC473243
0.8	Intermediate Similarity	NPC51292
0.8	Intermediate Similarity	NPC251854
0.8	Intermediate Similarity	NPC470753
0.8	Intermediate Similarity	NPC473220
0.8	Intermediate Similarity	NPC93084
0.8	Intermediate Similarity	NPC146351
0.8	Intermediate Similarity	NPC325497
0.7982	Intermediate Similarity	NPC56493
0.7982	Intermediate Similarity	NPC470391
0.7969	Intermediate Similarity	NPC239134
0.7966	Intermediate Similarity	NPC186933
0.7966	Intermediate Similarity	NPC474408
0.7966	Intermediate Similarity	NPC274839
0.7966	Intermediate Similarity	NPC306740
0.7966	Intermediate Similarity	NPC93181
0.7966	Intermediate Similarity	NPC470764
0.7965	Intermediate Similarity	NPC209632
0.7963	Intermediate Similarity	NPC260233
0.7949	Intermediate Similarity	NPC470253
0.7944	Intermediate Similarity	NPC153885
0.7937	Intermediate Similarity	NPC428300
0.7934	Intermediate Similarity	NPC204784
0.7931	Intermediate Similarity	NPC265513
0.792	Intermediate Similarity	NPC476599
0.7913	Intermediate Similarity	NPC469636
0.7909	Intermediate Similarity	NPC78701
0.7909	Intermediate Similarity	NPC225060
0.7909	Intermediate Similarity	NPC35448
0.7907	Intermediate Similarity	NPC183103
0.7899	Intermediate Similarity	NPC149691
0.7895	Intermediate Similarity	NPC119271
0.7895	Intermediate Similarity	NPC83409
0.7895	Intermediate Similarity	NPC185763
0.7886	Intermediate Similarity	NPC167323
0.7886	Intermediate Similarity	NPC269923
0.7881	Intermediate Similarity	NPC153053
0.7881	Intermediate Similarity	NPC67377
0.7876	Intermediate Similarity	NPC114594
0.787	Intermediate Similarity	NPC238219
0.7863	Intermediate Similarity	NPC280789
0.7863	Intermediate Similarity	NPC66208
0.7863	Intermediate Similarity	NPC471188
0.7857	Intermediate Similarity	NPC474737
0.7857	Intermediate Similarity	NPC188895
0.7851	Intermediate Similarity	NPC318173
0.785	Intermediate Similarity	NPC133461
0.7846	Intermediate Similarity	NPC59459
0.7846	Intermediate Similarity	NPC310662
0.7845	Intermediate Similarity	NPC273837
0.7845	Intermediate Similarity	NPC174099
0.7838	Intermediate Similarity	NPC203925
0.7829	Intermediate Similarity	NPC472394
0.7829	Intermediate Similarity	NPC279596
0.7829	Intermediate Similarity	NPC164295
0.7826	Intermediate Similarity	NPC203732
0.7823	Intermediate Similarity	NPC223351
0.7818	Intermediate Similarity	NPC265220
0.7818	Intermediate Similarity	NPC92754
0.7818	Intermediate Similarity	NPC276775
0.7818	Intermediate Similarity	NPC239185
0.7818	Intermediate Similarity	NPC249912
0.7812	Intermediate Similarity	NPC147561
0.7797	Intermediate Similarity	NPC272524
0.7797	Intermediate Similarity	NPC143768
0.7788	Intermediate Similarity	NPC89886
0.7788	Intermediate Similarity	NPC60679
0.7778	Intermediate Similarity	NPC155232
0.7778	Intermediate Similarity	NPC137315
0.7778	Intermediate Similarity	NPC275576
0.7769	Intermediate Similarity	NPC80605
0.7769	Intermediate Similarity	NPC323440
0.7769	Intermediate Similarity	NPC222968
0.7769	Intermediate Similarity	NPC476644
0.7768	Intermediate Similarity	NPC42211
0.7768	Intermediate Similarity	NPC245927
0.776	Intermediate Similarity	NPC472704
0.776	Intermediate Similarity	NPC328107
0.776	Intermediate Similarity	NPC318067
0.7759	Intermediate Similarity	NPC269023
0.7759	Intermediate Similarity	NPC192577
0.7759	Intermediate Similarity	NPC99846
0.7752	Intermediate Similarity	NPC469519
0.7748	Intermediate Similarity	NPC49994
0.7748	Intermediate Similarity	NPC134882
0.7748	Intermediate Similarity	NPC75724
0.7739	Intermediate Similarity	NPC30594
0.7739	Intermediate Similarity	NPC37622
0.7731	Intermediate Similarity	NPC308744
0.7727	Intermediate Similarity	NPC309056
0.7724	Intermediate Similarity	NPC476225
0.7719	Intermediate Similarity	NPC31786
0.7717	Intermediate Similarity	NPC169913
0.7712	Intermediate Similarity	NPC321852
0.771	Intermediate Similarity	NPC203486
0.7705	Intermediate Similarity	NPC254233
0.768	Intermediate Similarity	NPC472703
0.7679	Intermediate Similarity	NPC118343
0.7674	Intermediate Similarity	NPC57552
0.7674	Intermediate Similarity	NPC262819
0.7674	Intermediate Similarity	NPC471832
0.7674	Intermediate Similarity	NPC82712
0.7672	Intermediate Similarity	NPC112903
0.7669	Intermediate Similarity	NPC471670
0.7667	Intermediate Similarity	NPC217111
0.7667	Intermediate Similarity	NPC474685
0.7667	Intermediate Similarity	NPC215419
0.7667	Intermediate Similarity	NPC476357
0.7652	Intermediate Similarity	NPC471186
0.7652	Intermediate Similarity	NPC172483
0.7652	Intermediate Similarity	NPC269457
0.7652	Intermediate Similarity	NPC23894
0.7652	Intermediate Similarity	NPC212207
0.7652	Intermediate Similarity	NPC474659
0.7642	Intermediate Similarity	NPC202015
0.7636	Intermediate Similarity	NPC130398
0.7634	Intermediate Similarity	NPC472656
0.7634	Intermediate Similarity	NPC165612
0.7627	Intermediate Similarity	NPC475002
0.7627	Intermediate Similarity	NPC95126
0.7627	Intermediate Similarity	NPC260818
0.7615	Intermediate Similarity	NPC1682
0.7615	Intermediate Similarity	NPC188844
0.7615	Intermediate Similarity	NPC470278
0.7615	Intermediate Similarity	NPC253488
0.7615	Intermediate Similarity	NPC72915
0.7615	Intermediate Similarity	NPC323420
0.7611	Intermediate Similarity	NPC476993
0.7611	Intermediate Similarity	NPC109514
0.7607	Intermediate Similarity	NPC318327
0.7603	Intermediate Similarity	NPC100353
0.7603	Intermediate Similarity	NPC260886
0.7594	Intermediate Similarity	NPC472551
0.7594	Intermediate Similarity	NPC22644
0.7594	Intermediate Similarity	NPC472545
0.7593	Intermediate Similarity	NPC173413
0.7586	Intermediate Similarity	NPC37914
0.7583	Intermediate Similarity	NPC471721
0.7583	Intermediate Similarity	NPC241851
0.7581	Intermediate Similarity	NPC133302
0.7576	Intermediate Similarity	NPC474608
0.7576	Intermediate Similarity	NPC126516
0.7576	Intermediate Similarity	NPC470406
0.7576	Intermediate Similarity	NPC329913
0.7568	Intermediate Similarity	NPC185208
0.7568	Intermediate Similarity	NPC219573
0.7565	Intermediate Similarity	NPC329282
0.7563	Intermediate Similarity	NPC186128

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 NPC474095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	990
0.2-0.3	1130
0.3-0.4	2720
0.4-0.5	2423
0.5-0.6	1238
0.6-0.7	349
0.7-0.8	30
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8793	High Similarity	NPD3412	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD2182	Approved
0.7953	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3495	Discontinued
0.7815	Intermediate Similarity	NPD5951	Approved
0.7812	Intermediate Similarity	NPD7008	Discontinued
0.7719	Intermediate Similarity	NPD164	Approved
0.7679	Intermediate Similarity	NPD1238	Approved
0.7615	Intermediate Similarity	NPD7631	Approved
0.76	Intermediate Similarity	NPD6287	Discontinued
0.7581	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7609	Phase 3
0.7478	Intermediate Similarity	NPD1929	Approved
0.7478	Intermediate Similarity	NPD1930	Approved
0.7478	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7713	Phase 3
0.7422	Intermediate Similarity	NPD1876	Approved
0.7402	Intermediate Similarity	NPD3972	Approved
0.7368	Intermediate Similarity	NPD2066	Phase 3
0.736	Intermediate Similarity	NPD1651	Approved
0.7317	Intermediate Similarity	NPD3317	Approved
0.7315	Intermediate Similarity	NPD650	Approved
0.7299	Intermediate Similarity	NPD2346	Discontinued
0.7295	Intermediate Similarity	NPD1241	Discontinued
0.7286	Intermediate Similarity	NPD7236	Approved
0.7273	Intermediate Similarity	NPD6039	Approved
0.7265	Intermediate Similarity	NPD1237	Approved
0.7257	Intermediate Similarity	NPD1989	Approved
0.7213	Intermediate Similarity	NPD7094	Approved
0.7213	Intermediate Similarity	NPD6858	Approved
0.7188	Intermediate Similarity	NPD1281	Approved
0.7188	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2798	Approved
0.7153	Intermediate Similarity	NPD7239	Suspended
0.7143	Intermediate Similarity	NPD7009	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7132	Intermediate Similarity	NPD4878	Approved
0.7119	Intermediate Similarity	NPD5909	Discontinued
0.7111	Intermediate Similarity	NPD2979	Phase 3
0.7097	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD7610	Discontinued
0.705	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4198	Discontinued
0.7023	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD1087	Approved
0.6986	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3764	Approved
0.696	Remote Similarity	NPD2629	Approved
0.6949	Remote Similarity	NPD1932	Approved
0.694	Remote Similarity	NPD7055	Discontinued
0.693	Remote Similarity	NPD1202	Approved
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD9259	Approved
0.6909	Remote Similarity	NPD9257	Approved
0.6906	Remote Similarity	NPD2799	Discontinued
0.6899	Remote Similarity	NPD5125	Phase 3
0.6899	Remote Similarity	NPD5126	Approved
0.6899	Remote Similarity	NPD2932	Approved
0.6897	Remote Similarity	NPD6273	Approved
0.6894	Remote Similarity	NPD5667	Approved
0.6891	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2329	Discontinued
0.688	Remote Similarity	NPD6010	Discontinued
0.687	Remote Similarity	NPD6637	Approved
0.687	Remote Similarity	NPD1693	Approved
0.6861	Remote Similarity	NPD4307	Phase 2
0.6857	Remote Similarity	NPD2531	Phase 2
0.6857	Remote Similarity	NPD2438	Suspended
0.6846	Remote Similarity	NPD4879	Approved
0.6838	Remote Similarity	NPD2313	Discontinued
0.6829	Remote Similarity	NPD2067	Discontinued
0.6822	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3025	Approved
0.6822	Remote Similarity	NPD3024	Approved
0.6818	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5157	Phase 1
0.6818	Remote Similarity	NPD5159	Phase 2
0.6814	Remote Similarity	NPD1086	Approved
0.6814	Remote Similarity	NPD1090	Approved
0.6814	Remote Similarity	NPD3673	Approved
0.6814	Remote Similarity	NPD3672	Approved
0.6814	Remote Similarity	NPD1089	Approved
0.6794	Remote Similarity	NPD1201	Approved
0.6791	Remote Similarity	NPD4980	Approved
0.6788	Remote Similarity	NPD7961	Discontinued
0.6788	Remote Similarity	NPD8032	Phase 2
0.6786	Remote Similarity	NPD3748	Approved
0.6783	Remote Similarity	NPD8166	Discontinued
0.6783	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2201	Approved
0.6769	Remote Similarity	NPD3019	Approved
0.6769	Remote Similarity	NPD4626	Approved
0.6767	Remote Similarity	NPD2198	Approved
0.6767	Remote Similarity	NPD2199	Approved
0.6763	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7458	Discontinued
0.6755	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6647	Phase 2
0.6744	Remote Similarity	NPD9545	Approved
0.6744	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7741	Discontinued
0.6739	Remote Similarity	NPD3373	Approved
0.6739	Remote Similarity	NPD3142	Approved
0.6739	Remote Similarity	NPD3140	Approved
0.6738	Remote Similarity	NPD2796	Approved
0.6736	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD800	Approved
0.6724	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3026	Approved
0.6718	Remote Similarity	NPD3023	Approved
0.6716	Remote Similarity	NPD1470	Approved
0.6714	Remote Similarity	NPD2567	Approved
0.6714	Remote Similarity	NPD2569	Approved
0.6713	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7057	Phase 3
0.6711	Remote Similarity	NPD7058	Phase 2
0.6696	Remote Similarity	NPD1508	Approved
0.6696	Remote Similarity	NPD1088	Approved
0.6694	Remote Similarity	NPD3047	Approved
0.6694	Remote Similarity	NPD5237	Approved
0.6694	Remote Similarity	NPD3048	Approved
0.6694	Remote Similarity	NPD5235	Approved
0.6694	Remote Similarity	NPD5236	Approved
0.6694	Remote Similarity	NPD5239	Approved
0.6694	Remote Similarity	NPD3046	Approved
0.6694	Remote Similarity	NPD5240	Approved
0.6692	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6832	Phase 2
0.669	Remote Similarity	NPD7611	Approved
0.669	Remote Similarity	NPD1471	Phase 3
0.6689	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD4308	Phase 3
0.6644	Remote Similarity	NPD3226	Approved
0.6641	Remote Similarity	NPD5306	Approved
0.6641	Remote Similarity	NPD5305	Approved
0.6638	Remote Similarity	NPD1563	Approved
0.662	Remote Similarity	NPD6100	Approved
0.662	Remote Similarity	NPD6099	Approved
0.6606	Remote Similarity	NPD942	Approved
0.6593	Remote Similarity	NPD3266	Approved
0.6593	Remote Similarity	NPD2797	Approved
0.6593	Remote Similarity	NPD3267	Approved
0.6591	Remote Similarity	NPD3895	Approved
0.6591	Remote Similarity	NPD3897	Approved
0.6591	Remote Similarity	NPD3896	Approved
0.6591	Remote Similarity	NPD3898	Approved
0.6589	Remote Similarity	NPD9493	Approved
0.6585	Remote Similarity	NPD3134	Approved
0.656	Remote Similarity	NPD1317	Discontinued
0.6555	Remote Similarity	NPD5926	Approved
0.6552	Remote Similarity	NPD3750	Approved
0.6549	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6663	Approved
0.6544	Remote Similarity	NPD2788	Approved
0.6541	Remote Similarity	NPD4806	Approved
0.6541	Remote Similarity	NPD4807	Approved
0.6538	Remote Similarity	NPD7644	Approved
0.6529	Remote Similarity	NPD2193	Phase 2
0.6529	Remote Similarity	NPD2648	Phase 3
0.6525	Remote Similarity	NPD1843	Approved
0.6522	Remote Similarity	NPD6966	Discovery
0.6515	Remote Similarity	NPD17	Approved
0.6515	Remote Similarity	NPD2345	Approved
0.6503	Remote Similarity	NPD4477	Approved
0.6503	Remote Similarity	NPD2935	Discontinued
0.6503	Remote Similarity	NPD5408	Approved
0.6503	Remote Similarity	NPD4476	Approved
0.6503	Remote Similarity	NPD5406	Approved
0.6503	Remote Similarity	NPD5404	Approved
0.6503	Remote Similarity	NPD5405	Approved
0.6496	Remote Similarity	NPD5736	Approved
0.6496	Remote Similarity	NPD7084	Phase 3
0.6486	Remote Similarity	NPD2533	Approved
0.6486	Remote Similarity	NPD2532	Approved
0.6486	Remote Similarity	NPD2534	Approved
0.6486	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3268	Approved
0.6471	Remote Similarity	NPD1566	Phase 3
0.6471	Remote Similarity	NPD1565	Approved
0.6471	Remote Similarity	NPD1564	Approved
0.6466	Remote Similarity	NPD4106	Approved
0.6466	Remote Similarity	NPD1239	Approved
0.6466	Remote Similarity	NPD4135	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