NPASS Compound

Structure

CID295664 OpenBabel06191716102D 27 29 0 0 0 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7321 -2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2321 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7321 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -2.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 -0.8660 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2321 0.1340 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 14 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 12 17 1 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 13 27 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 23 2 0 0 0 0 19 20 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.13
Volume:	380.985
LogP:	4.019
LogD:	3.008
LogS:	-5.117
# Rotatable Bonds:	6
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	2.936
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.68
MDCK Permeability:	2.5680874387035146e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	101.0066146850586%
Volume Distribution (VD):	0.595
Pgp-substrate:	0.5583959817886353%

ADMET: Metabolism

CYP1A2-inhibitor:	0.672
CYP1A2-substrate:	0.417
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	2.249
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.607
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.055
Carcinogencity:	0.572
Eye Corrosion:	0.003
Eye Irritation:	0.136
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC295664

Natural Product ID:	NPC295664
*Common Name:**	OYMXVGBCNMQSNT-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OYMXVGBCNMQSNT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H20O5/c1-22(2,13-27-21(26)14-8-4-3-5-9-14)12-17-18(23)15-10-6-7-11-16(15)19(24)20(17)25/h3-11,25H,12-13H2,1-2H3/p-1
SMILES:	CC(C)(CC1=C(C(=O)c2ccccc2C1=O)[O-])COC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL188174
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8463799]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792629]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214738]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14480	Tornabea scutellifera	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12707	Lithospermum canescens	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11678	Aeonium cuneatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13891	Scolytus multistriatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11855	Streptomyces xanthocidicus	Species	Streptomycetaceae	Bacteria	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	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1530.0	nM	PMID[478964]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3020.0	nM	PMID[478964]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4850.0	nM	PMID[478964]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	48640.0	nM	PMID[478964]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3020.0	nM	PMID[478965]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1530.0	nM	PMID[478965]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4850.0	nM	PMID[478965]

☑ 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 NPC295664 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	231
0.1-0.2	1099
0.2-0.3	2493
0.3-0.4	6122
0.4-0.5	12056
0.5-0.6	9679
0.6-0.7	9527
0.7-0.8	1404
0.8-0.85	81
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC204784
0.8819	High Similarity	NPC471832
0.879	High Similarity	NPC328107
0.864	High Similarity	NPC318067
0.8516	High Similarity	NPC51448
0.8516	High Similarity	NPC115797
0.85	High Similarity	NPC196075
0.8468	Intermediate Similarity	NPC473243
0.8403	Intermediate Similarity	NPC210089
0.8374	Intermediate Similarity	NPC222968
0.8374	Intermediate Similarity	NPC323440
0.8374	Intermediate Similarity	NPC80605
0.8359	Intermediate Similarity	NPC275576
0.8359	Intermediate Similarity	NPC470765
0.8347	Intermediate Similarity	NPC153053
0.8346	Intermediate Similarity	NPC85511
0.8346	Intermediate Similarity	NPC51079
0.8333	Intermediate Similarity	NPC321852
0.8333	Intermediate Similarity	NPC79496
0.832	Intermediate Similarity	NPC77000
0.832	Intermediate Similarity	NPC238861
0.8306	Intermediate Similarity	NPC318173
0.8295	Intermediate Similarity	NPC473220
0.8295	Intermediate Similarity	NPC470753
0.8295	Intermediate Similarity	NPC169913
0.8279	Intermediate Similarity	NPC474408
0.8279	Intermediate Similarity	NPC228936
0.8271	Intermediate Similarity	NPC329913
0.8271	Intermediate Similarity	NPC126516
0.8271	Intermediate Similarity	NPC203486
0.8264	Intermediate Similarity	NPC143768
0.8254	Intermediate Similarity	NPC144547
0.825	Intermediate Similarity	NPC260818
0.825	Intermediate Similarity	NPC137315
0.824	Intermediate Similarity	NPC202015
0.8235	Intermediate Similarity	NPC469636
0.8235	Intermediate Similarity	NPC10251
0.8235	Intermediate Similarity	NPC17417
0.8226	Intermediate Similarity	NPC45794
0.8217	Intermediate Similarity	NPC476599
0.8211	Intermediate Similarity	NPC226093
0.8203	Intermediate Similarity	NPC472704
0.8197	Intermediate Similarity	NPC326664
0.8189	Intermediate Similarity	NPC167323
0.8189	Intermediate Similarity	NPC269923
0.8182	Intermediate Similarity	NPC82899
0.8182	Intermediate Similarity	NPC270699
0.8175	Intermediate Similarity	NPC988
0.8175	Intermediate Similarity	NPC232958
0.8175	Intermediate Similarity	NPC289432
0.8167	Intermediate Similarity	NPC93084
0.8167	Intermediate Similarity	NPC251854
0.8167	Intermediate Similarity	NPC196246
0.8167	Intermediate Similarity	NPC214067
0.8151	Intermediate Similarity	NPC470391
0.8151	Intermediate Similarity	NPC56493
0.8145	Intermediate Similarity	NPC158157
0.813	Intermediate Similarity	NPC221275
0.813	Intermediate Similarity	NPC474095
0.813	Intermediate Similarity	NPC306740
0.813	Intermediate Similarity	NPC210092
0.8125	Intermediate Similarity	NPC472703
0.8125	Intermediate Similarity	NPC223351
0.812	Intermediate Similarity	NPC301943
0.812	Intermediate Similarity	NPC474365
0.812	Intermediate Similarity	NPC274443
0.8115	Intermediate Similarity	NPC272524
0.8115	Intermediate Similarity	NPC128368
0.8115	Intermediate Similarity	NPC13784
0.811	Intermediate Similarity	NPC472981
0.811	Intermediate Similarity	NPC50872
0.8099	Intermediate Similarity	NPC305912
0.8099	Intermediate Similarity	NPC291799
0.8099	Intermediate Similarity	NPC474157
0.8099	Intermediate Similarity	NPC1082
0.8083	Intermediate Similarity	NPC85493
0.8074	Intermediate Similarity	NPC212207
0.8067	Intermediate Similarity	NPC119271
0.8065	Intermediate Similarity	NPC135730
0.8062	Intermediate Similarity	NPC12881
0.8062	Intermediate Similarity	NPC228739
0.8062	Intermediate Similarity	NPC140118
0.8051	Intermediate Similarity	NPC329282
0.8049	Intermediate Similarity	NPC196673
0.8049	Intermediate Similarity	NPC477411
0.8049	Intermediate Similarity	NPC307651
0.8049	Intermediate Similarity	NPC471721
0.8045	Intermediate Similarity	NPC72915
0.8043	Intermediate Similarity	NPC213567
0.8034	Intermediate Similarity	NPC244427
0.8034	Intermediate Similarity	NPC222390
0.8033	Intermediate Similarity	NPC292834
0.8033	Intermediate Similarity	NPC212415
0.8017	Intermediate Similarity	NPC174099
0.8016	Intermediate Similarity	NPC254233
0.8015	Intermediate Similarity	NPC309056
0.8015	Intermediate Similarity	NPC472372
0.8015	Intermediate Similarity	NPC472545
0.8015	Intermediate Similarity	NPC472551
0.8015	Intermediate Similarity	NPC472374
0.8015	Intermediate Similarity	NPC51292
0.8	Intermediate Similarity	NPC469843
0.8	Intermediate Similarity	NPC310662
0.8	Intermediate Similarity	NPC48929
0.7986	Intermediate Similarity	NPC472546
0.7986	Intermediate Similarity	NPC182869
0.7986	Intermediate Similarity	NPC183540
0.7985	Intermediate Similarity	NPC472394
0.7984	Intermediate Similarity	NPC65627
0.7984	Intermediate Similarity	NPC470764
0.7984	Intermediate Similarity	NPC474685
0.7983	Intermediate Similarity	NPC209632
0.7983	Intermediate Similarity	NPC172483
0.7983	Intermediate Similarity	NPC269457
0.797	Intermediate Similarity	NPC272946
0.7959	Intermediate Similarity	NPC3898
0.7956	Intermediate Similarity	NPC39549
0.7955	Intermediate Similarity	NPC472707
0.7953	Intermediate Similarity	NPC472708
0.7951	Intermediate Similarity	NPC167504
0.7949	Intermediate Similarity	NPC42211
0.7943	Intermediate Similarity	NPC127857
0.7943	Intermediate Similarity	NPC476473
0.7941	Intermediate Similarity	NPC477893
0.7941	Intermediate Similarity	NPC477896
0.7941	Intermediate Similarity	NPC194970
0.7941	Intermediate Similarity	NPC23894
0.7939	Intermediate Similarity	NPC137416
0.7939	Intermediate Similarity	NPC236405
0.7937	Intermediate Similarity	NPC228318
0.7937	Intermediate Similarity	NPC152812
0.7934	Intermediate Similarity	NPC265407
0.7934	Intermediate Similarity	NPC83628
0.7926	Intermediate Similarity	NPC472656
0.792	Intermediate Similarity	NPC471616
0.7917	Intermediate Similarity	NPC306799
0.7917	Intermediate Similarity	NPC101043
0.7914	Intermediate Similarity	NPC224491
0.7903	Intermediate Similarity	NPC241851
0.7899	Intermediate Similarity	NPC114594
0.7899	Intermediate Similarity	NPC31786
0.7891	Intermediate Similarity	NPC475827
0.7891	Intermediate Similarity	NPC474223
0.7886	Intermediate Similarity	NPC66208
0.7886	Intermediate Similarity	NPC158282
0.7879	Intermediate Similarity	NPC472706
0.7872	Intermediate Similarity	NPC474300
0.7869	Intermediate Similarity	NPC273837
0.7863	Intermediate Similarity	NPC246166
0.7863	Intermediate Similarity	NPC118343
0.7852	Intermediate Similarity	NPC67197
0.7847	Intermediate Similarity	NPC112216
0.7847	Intermediate Similarity	NPC165260
0.7847	Intermediate Similarity	NPC198455
0.7847	Intermediate Similarity	NPC161239
0.7842	Intermediate Similarity	NPC472547
0.784	Intermediate Similarity	NPC217111
0.784	Intermediate Similarity	NPC93181
0.7836	Intermediate Similarity	NPC473247
0.7836	Intermediate Similarity	NPC82712
0.7836	Intermediate Similarity	NPC147561
0.7836	Intermediate Similarity	NPC131684
0.7833	Intermediate Similarity	NPC134120
0.7826	Intermediate Similarity	NPC471670
0.7823	Intermediate Similarity	NPC161611
0.7823	Intermediate Similarity	NPC470253
0.7823	Intermediate Similarity	NPC93287
0.782	Intermediate Similarity	NPC478162
0.782	Intermediate Similarity	NPC478165
0.7815	Intermediate Similarity	NPC255676
0.7815	Intermediate Similarity	NPC60679
0.781	Intermediate Similarity	NPC474659
0.7808	Intermediate Similarity	NPC77719
0.7805	Intermediate Similarity	NPC476003
0.7805	Intermediate Similarity	NPC265513
0.7803	Intermediate Similarity	NPC9180
0.7803	Intermediate Similarity	NPC100402
0.7801	Intermediate Similarity	NPC477468
0.78	Intermediate Similarity	NPC68619
0.7794	Intermediate Similarity	NPC477364
0.7787	Intermediate Similarity	NPC192577
0.7787	Intermediate Similarity	NPC99846
0.7787	Intermediate Similarity	NPC318327
0.7787	Intermediate Similarity	NPC269023
0.7786	Intermediate Similarity	NPC295339
0.7778	Intermediate Similarity	NPC250046
0.7778	Intermediate Similarity	NPC60509
0.7778	Intermediate Similarity	NPC470278
0.7778	Intermediate Similarity	NPC81698
0.7778	Intermediate Similarity	NPC27659
0.7778	Intermediate Similarity	NPC78701
0.7778	Intermediate Similarity	NPC473215
0.7778	Intermediate Similarity	NPC35448
0.777	Intermediate Similarity	NPC472371
0.777	Intermediate Similarity	NPC472395
0.7769	Intermediate Similarity	NPC37622
0.7769	Intermediate Similarity	NPC30594
0.776	Intermediate Similarity	NPC308744
0.776	Intermediate Similarity	NPC474363
0.7755	Intermediate Similarity	NPC112523

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 NPC295664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	802
0.2-0.3	1193
0.3-0.4	2359
0.4-0.5	2527
0.5-0.6	1462
0.6-0.7	515
0.7-0.8	73
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8527	High Similarity	NPD5952	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD5951	Approved
0.8244	Intermediate Similarity	NPD7008	Discontinued
0.8235	Intermediate Similarity	NPD2182	Approved
0.8099	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD7236	Approved
0.8033	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6287	Discontinued
0.7899	Intermediate Similarity	NPD164	Approved
0.7863	Intermediate Similarity	NPD1238	Approved
0.7793	Intermediate Similarity	NPD7239	Suspended
0.7778	Intermediate Similarity	NPD4198	Discontinued
0.775	Intermediate Similarity	NPD1237	Approved
0.7714	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD2629	Approved
0.7698	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1930	Approved
0.7667	Intermediate Similarity	NPD1929	Approved
0.7667	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD5909	Discontinued
0.7589	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD3972	Approved
0.7563	Intermediate Similarity	NPD2066	Phase 3
0.7557	Intermediate Similarity	NPD4879	Approved
0.7552	Intermediate Similarity	NPD4628	Phase 3
0.7552	Intermediate Similarity	NPD7003	Approved
0.7534	Intermediate Similarity	NPD6273	Approved
0.7518	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7961	Discontinued
0.7444	Intermediate Similarity	NPD4878	Approved
0.7438	Intermediate Similarity	NPD1932	Approved
0.7434	Intermediate Similarity	NPD7058	Phase 2
0.7434	Intermediate Similarity	NPD7057	Phase 3
0.7431	Intermediate Similarity	NPD8166	Discontinued
0.7424	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD7458	Discontinued
0.7381	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6010	Discontinued
0.7343	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6599	Discontinued
0.7328	Intermediate Similarity	NPD9545	Approved
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7311	Intermediate Similarity	NPD1989	Approved
0.7302	Intermediate Similarity	NPD2067	Discontinued
0.7288	Intermediate Similarity	NPD1202	Approved
0.7288	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3226	Approved
0.7266	Intermediate Similarity	NPD3268	Approved
0.7266	Intermediate Similarity	NPD7094	Approved
0.7266	Intermediate Similarity	NPD6858	Approved
0.725	Intermediate Similarity	NPD3495	Discontinued
0.7226	Intermediate Similarity	NPD2798	Approved
0.7222	Intermediate Similarity	NPD2329	Discontinued
0.7214	Intermediate Similarity	NPD7713	Phase 3
0.7206	Intermediate Similarity	NPD1283	Approved
0.7206	Intermediate Similarity	NPD1876	Approved
0.7192	Intermediate Similarity	NPD3750	Approved
0.719	Intermediate Similarity	NPD7819	Suspended
0.7164	Intermediate Similarity	NPD4136	Approved
0.7164	Intermediate Similarity	NPD4106	Approved
0.7164	Intermediate Similarity	NPD4135	Approved
0.7153	Intermediate Similarity	NPD2797	Approved
0.7153	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7122	Intermediate Similarity	NPD6832	Phase 2
0.7119	Intermediate Similarity	NPD7609	Phase 3
0.7103	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD6647	Phase 2
0.7092	Intermediate Similarity	NPD6663	Approved
0.709	Intermediate Similarity	NPD5305	Approved
0.709	Intermediate Similarity	NPD2932	Approved
0.709	Intermediate Similarity	NPD5306	Approved
0.7083	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4308	Phase 3
0.708	Intermediate Similarity	NPD5667	Approved
0.7078	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1088	Approved
0.7059	Intermediate Similarity	NPD7631	Approved
0.705	Intermediate Similarity	NPD5736	Approved
0.7049	Intermediate Similarity	NPD9495	Approved
0.7047	Intermediate Similarity	NPD6799	Approved
0.7045	Intermediate Similarity	NPD9493	Approved
0.7042	Intermediate Similarity	NPD2979	Phase 3
0.7034	Intermediate Similarity	NPD9258	Approved
0.7034	Intermediate Similarity	NPD2935	Discontinued
0.7034	Intermediate Similarity	NPD9256	Approved
0.7029	Intermediate Similarity	NPD3266	Approved
0.7029	Intermediate Similarity	NPD3267	Approved
0.7027	Intermediate Similarity	NPD2354	Approved
0.7027	Intermediate Similarity	NPD3887	Approved
0.7019	Intermediate Similarity	NPD7799	Discontinued
0.7015	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4102	Approved
0.7015	Intermediate Similarity	NPD4105	Approved
0.6993	Remote Similarity	NPD6355	Discontinued
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4806	Approved
0.6985	Remote Similarity	NPD4807	Approved
0.6985	Remote Similarity	NPD1201	Approved
0.6985	Remote Similarity	NPD1281	Approved
0.6975	Remote Similarity	NPD1239	Approved
0.6972	Remote Similarity	NPD6233	Phase 2
0.6972	Remote Similarity	NPD8032	Phase 2
0.6963	Remote Similarity	NPD3019	Approved
0.6954	Remote Similarity	NPD5049	Phase 3
0.695	Remote Similarity	NPD7095	Approved
0.6948	Remote Similarity	NPD7411	Suspended
0.6947	Remote Similarity	NPD1241	Discontinued
0.6946	Remote Similarity	NPD8434	Phase 2
0.6943	Remote Similarity	NPD7075	Discontinued
0.6942	Remote Similarity	NPD1693	Approved
0.694	Remote Similarity	NPD7009	Phase 2
0.694	Remote Similarity	NPD1894	Discontinued
0.6934	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD650	Approved
0.6923	Remote Similarity	NPD4307	Phase 2
0.6918	Remote Similarity	NPD5406	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD5408	Approved
0.6918	Remote Similarity	NPD5405	Approved
0.6918	Remote Similarity	NPD5404	Approved
0.6906	Remote Similarity	NPD1203	Approved
0.6903	Remote Similarity	NPD6801	Discontinued
0.6891	Remote Similarity	NPD1086	Approved
0.6891	Remote Similarity	NPD1089	Approved
0.6891	Remote Similarity	NPD1090	Approved
0.6889	Remote Similarity	NPD1651	Approved
0.6887	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5159	Phase 2
0.6884	Remote Similarity	NPD5157	Phase 1
0.6884	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5203	Approved
0.6879	Remote Similarity	NPD5201	Approved
0.6879	Remote Similarity	NPD4617	Approved
0.6879	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4620	Approved
0.6871	Remote Similarity	NPD2353	Approved
0.6871	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7610	Discontinued
0.6853	Remote Similarity	NPD4062	Phase 3
0.685	Remote Similarity	NPD5048	Discontinued
0.6849	Remote Similarity	NPD7305	Phase 1
0.6848	Remote Similarity	NPD8368	Discontinued
0.6846	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9259	Approved
0.6838	Remote Similarity	NPD5125	Phase 3
0.6838	Remote Similarity	NPD5126	Approved
0.6838	Remote Similarity	NPD9257	Approved
0.6835	Remote Similarity	NPD2198	Approved
0.6835	Remote Similarity	NPD2199	Approved
0.6831	Remote Similarity	NPD6039	Approved
0.6829	Remote Similarity	NPD1566	Phase 3
0.6829	Remote Similarity	NPD1565	Approved
0.6829	Remote Similarity	NPD1564	Approved
0.6824	Remote Similarity	NPD4534	Discontinued
0.6812	Remote Similarity	NPD9717	Approved
0.6809	Remote Similarity	NPD5204	Approved
0.6807	Remote Similarity	NPD800	Approved
0.6806	Remote Similarity	NPD4140	Approved
0.6806	Remote Similarity	NPD4060	Phase 1
0.6806	Remote Similarity	NPD3373	Approved
0.6803	Remote Similarity	NPD2531	Phase 2
0.6803	Remote Similarity	NPD2438	Suspended
0.6797	Remote Similarity	NPD5403	Approved
0.6791	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3023	Approved
0.6788	Remote Similarity	NPD3847	Discontinued
0.6788	Remote Similarity	NPD3026	Approved
0.6783	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5401	Approved
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1317	Discontinued
0.6768	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3024	Approved
0.6765	Remote Similarity	NPD5585	Approved
0.6765	Remote Similarity	NPD5691	Approved
0.6765	Remote Similarity	NPD3025	Approved
0.6763	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2344	Approved
0.6755	Remote Similarity	NPD7440	Discontinued
0.6747	Remote Similarity	NPD6765	Approved
0.6747	Remote Similarity	NPD6764	Approved
0.6746	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8150	Discontinued
0.6739	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2788	Approved
0.6738	Remote Similarity	NPD6085	Phase 2
0.6736	Remote Similarity	NPD7715	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