NPASS Compound

Structure

CID204784 OpenBabel06191715592D 30 31 0 0 0 0 0 0 0 0999 V2000 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 0.1340 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 2.5981 -1.5000 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 -0.8660 -1.5000 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 -6.9282 -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 1.7321 -1.0000 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 -0.0000 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 14 25 1 0 0 0 0 15 25 1 0 0 0 0 15 30 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 21 26 2 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.21
Volume:	444.066
LogP:	4.745
LogD:	3.739
LogS:	-5.976
# Rotatable Bonds:	9
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	4.069
Fsp3:	0.44
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:	-4.589
MDCK Permeability:	2.126481012965087e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	98.31351470947266%
Volume Distribution (VD):	0.608
Pgp-substrate:	0.8866373300552368%

ADMET: Metabolism

CYP1A2-inhibitor:	0.739
CYP1A2-substrate:	0.255
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.223
CYP2C9-inhibitor:	0.921
CYP2C9-substrate:	0.599
CYP2D6-inhibitor:	0.608
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	3.686
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.062
Carcinogencity:	0.167
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC204784

Natural Product ID:	NPC204784
*Common Name:**	Rhinacanthin C
IUPAC Name:	n.a.
Synonyms:	Rhinacanthin-C
Standard InCHIKey:	HBWJZSWEQJLURT-QIGLBIQCSA-N
Standard InCHI:	InChI=1S/C25H30O5/c1-6-16(2)10-9-11-17(3)24(29)30-15-25(4,5)14-20-21(26)18-12-7-8-13-19(18)22(27)23(20)28/h6-8,11-13,28H,9-10,14-15H2,1-5H3/b16-6+,17-11+
SMILES:	C/C=C(/CC/C=C(/C(=O)OCC(CC1=C(O)C(=O)c2c(C1=O)cccc2)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462962
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]
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]
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]

☑ 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
EC50	3
ED50	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1795	Organism	Murid herpesvirus 1	Murid herpesvirus 1	EC50	=	1.1	ug.mL-1	PMID[454558]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	EC50	=	0.02	ug.mL-1	PMID[454558]
NPT1795	Organism	Murid herpesvirus 1	Murid herpesvirus 1	EC50	=	0.57	ug.mL-1	PMID[454558]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	ED50	=	0.2	ppm	PMID[454559]

☑ 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 NPC204784 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	220
0.1-0.2	993
0.2-0.3	2311
0.3-0.4	6219
0.4-0.5	11595
0.5-0.6	13449
0.6-0.7	6930
0.7-0.8	911
0.8-0.85	63
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC295664
0.8917	High Similarity	NPC328107
0.8607	High Similarity	NPC318067
0.8584	High Similarity	NPC470391
0.8559	High Similarity	NPC274443
0.8522	High Similarity	NPC137315
0.8492	Intermediate Similarity	NPC471832
0.8487	Intermediate Similarity	NPC323440
0.8487	Intermediate Similarity	NPC80605
0.8487	Intermediate Similarity	NPC222968
0.8482	Intermediate Similarity	NPC329282
0.8468	Intermediate Similarity	NPC244427
0.8468	Intermediate Similarity	NPC222390
0.8448	Intermediate Similarity	NPC292834
0.8407	Intermediate Similarity	NPC172483
0.839	Intermediate Similarity	NPC470764
0.8376	Intermediate Similarity	NPC143768
0.8362	Intermediate Similarity	NPC291799
0.8362	Intermediate Similarity	NPC210089
0.8347	Intermediate Similarity	NPC202015
0.8333	Intermediate Similarity	NPC51448
0.8333	Intermediate Similarity	NPC115797
0.832	Intermediate Similarity	NPC236405
0.8305	Intermediate Similarity	NPC153053
0.8305	Intermediate Similarity	NPC241851
0.8305	Intermediate Similarity	NPC326664
0.8305	Intermediate Similarity	NPC196075
0.8291	Intermediate Similarity	NPC321852
0.8279	Intermediate Similarity	NPC473243
0.8264	Intermediate Similarity	NPC318173
0.825	Intermediate Similarity	NPC469843
0.8235	Intermediate Similarity	NPC217111
0.8226	Intermediate Similarity	NPC65627
0.8205	Intermediate Similarity	NPC260818
0.819	Intermediate Similarity	NPC10251
0.819	Intermediate Similarity	NPC17417
0.819	Intermediate Similarity	NPC469636
0.8175	Intermediate Similarity	NPC476599
0.8167	Intermediate Similarity	NPC226093
0.816	Intermediate Similarity	NPC140118
0.816	Intermediate Similarity	NPC12881
0.816	Intermediate Similarity	NPC472704
0.816	Intermediate Similarity	NPC85511
0.8151	Intermediate Similarity	NPC471721
0.8136	Intermediate Similarity	NPC82899
0.8136	Intermediate Similarity	NPC270699
0.813	Intermediate Similarity	NPC474223
0.813	Intermediate Similarity	NPC105709
0.813	Intermediate Similarity	NPC475827
0.812	Intermediate Similarity	NPC251854
0.812	Intermediate Similarity	NPC93084
0.812	Intermediate Similarity	NPC196246
0.812	Intermediate Similarity	NPC214067
0.8108	Intermediate Similarity	NPC156021
0.8103	Intermediate Similarity	NPC56493
0.8083	Intermediate Similarity	NPC228936
0.8083	Intermediate Similarity	NPC210092
0.8083	Intermediate Similarity	NPC306740
0.808	Intermediate Similarity	NPC472703
0.808	Intermediate Similarity	NPC223351
0.807	Intermediate Similarity	NPC474365
0.807	Intermediate Similarity	NPC301943
0.8067	Intermediate Similarity	NPC272524
0.8065	Intermediate Similarity	NPC50872
0.8053	Intermediate Similarity	NPC112552
0.8051	Intermediate Similarity	NPC474157
0.8051	Intermediate Similarity	NPC1082
0.8051	Intermediate Similarity	NPC305912
0.8049	Intermediate Similarity	NPC472708
0.8034	Intermediate Similarity	NPC192577
0.8034	Intermediate Similarity	NPC85493
0.8033	Intermediate Similarity	NPC152812
0.8031	Intermediate Similarity	NPC275576
0.8031	Intermediate Similarity	NPC470765
0.8017	Intermediate Similarity	NPC100767
0.8017	Intermediate Similarity	NPC119271
0.8016	Intermediate Similarity	NPC228739
0.8016	Intermediate Similarity	NPC51079
0.8	Intermediate Similarity	NPC477411
0.8	Intermediate Similarity	NPC167323
0.8	Intermediate Similarity	NPC269923
0.8	Intermediate Similarity	NPC307651
0.7984	Intermediate Similarity	NPC77000
0.7984	Intermediate Similarity	NPC238861
0.7969	Intermediate Similarity	NPC81135
0.7969	Intermediate Similarity	NPC470753
0.7969	Intermediate Similarity	NPC473220
0.7969	Intermediate Similarity	NPC169913
0.7966	Intermediate Similarity	NPC174099
0.7955	Intermediate Similarity	NPC126516
0.7955	Intermediate Similarity	NPC203486
0.7955	Intermediate Similarity	NPC329913
0.7937	Intermediate Similarity	NPC474254
0.7937	Intermediate Similarity	NPC474159
0.7934	Intermediate Similarity	NPC93181
0.7934	Intermediate Similarity	NPC474685
0.7934	Intermediate Similarity	NPC474095
0.7931	Intermediate Similarity	NPC209632
0.7923	Intermediate Similarity	NPC272946
0.792	Intermediate Similarity	NPC472981
0.7917	Intermediate Similarity	NPC470253
0.7917	Intermediate Similarity	NPC13784
0.7917	Intermediate Similarity	NPC128368
0.7917	Intermediate Similarity	NPC93287
0.7907	Intermediate Similarity	NPC472707
0.7899	Intermediate Similarity	NPC167504
0.7899	Intermediate Similarity	NPC265513
0.7886	Intermediate Similarity	NPC45794
0.7881	Intermediate Similarity	NPC83628
0.7881	Intermediate Similarity	NPC265407
0.7869	Intermediate Similarity	NPC135730
0.7845	Intermediate Similarity	NPC114594
0.7845	Intermediate Similarity	NPC31786
0.784	Intermediate Similarity	NPC475804
0.784	Intermediate Similarity	NPC476225
0.784	Intermediate Similarity	NPC474222
0.7833	Intermediate Similarity	NPC79496
0.7833	Intermediate Similarity	NPC218855
0.7833	Intermediate Similarity	NPC280789
0.7833	Intermediate Similarity	NPC212415
0.7829	Intermediate Similarity	NPC472706
0.7829	Intermediate Similarity	NPC51292
0.7812	Intermediate Similarity	NPC246166
0.781	Intermediate Similarity	NPC183540
0.7805	Intermediate Similarity	NPC158157
0.7797	Intermediate Similarity	NPC20485
0.7787	Intermediate Similarity	NPC474408
0.7787	Intermediate Similarity	NPC221275
0.7786	Intermediate Similarity	NPC82712
0.7778	Intermediate Similarity	NPC144547
0.7778	Intermediate Similarity	NPC134120
0.7769	Intermediate Similarity	NPC471481
0.7769	Intermediate Similarity	NPC478162
0.7769	Intermediate Similarity	NPC478165
0.7769	Intermediate Similarity	NPC161611
0.7761	Intermediate Similarity	NPC212207
0.7761	Intermediate Similarity	NPC194970
0.7761	Intermediate Similarity	NPC23894
0.776	Intermediate Similarity	NPC476645
0.7759	Intermediate Similarity	NPC329556
0.7759	Intermediate Similarity	NPC247976
0.7759	Intermediate Similarity	NPC60679
0.7752	Intermediate Similarity	NPC137416
0.775	Intermediate Similarity	NPC476003
0.775	Intermediate Similarity	NPC474057
0.7744	Intermediate Similarity	NPC15850
0.7744	Intermediate Similarity	NPC477364
0.7737	Intermediate Similarity	NPC256463
0.7737	Intermediate Similarity	NPC295339
0.7737	Intermediate Similarity	NPC306835
0.7737	Intermediate Similarity	NPC299405
0.7737	Intermediate Similarity	NPC29771
0.7737	Intermediate Similarity	NPC216312
0.7737	Intermediate Similarity	NPC111422
0.7737	Intermediate Similarity	NPC476477
0.7737	Intermediate Similarity	NPC471602
0.7734	Intermediate Similarity	NPC477362
0.7731	Intermediate Similarity	NPC269023
0.7731	Intermediate Similarity	NPC99846
0.7727	Intermediate Similarity	NPC72915
0.7724	Intermediate Similarity	NPC471616
0.7719	Intermediate Similarity	NPC35448
0.7719	Intermediate Similarity	NPC78701
0.7719	Intermediate Similarity	NPC229242
0.7712	Intermediate Similarity	NPC30594
0.7712	Intermediate Similarity	NPC37622
0.771	Intermediate Similarity	NPC225103
0.7705	Intermediate Similarity	NPC130591
0.7705	Intermediate Similarity	NPC308744
0.7705	Intermediate Similarity	NPC474363
0.7705	Intermediate Similarity	NPC234637
0.7705	Intermediate Similarity	NPC196673
0.7704	Intermediate Similarity	NPC472372
0.7704	Intermediate Similarity	NPC472551
0.7704	Intermediate Similarity	NPC472545
0.7704	Intermediate Similarity	NPC472374
0.7698	Intermediate Similarity	NPC232958
0.7698	Intermediate Similarity	NPC289432
0.7698	Intermediate Similarity	NPC988
0.7692	Intermediate Similarity	NPC110211
0.7692	Intermediate Similarity	NPC204579
0.7687	Intermediate Similarity	NPC477368
0.7687	Intermediate Similarity	NPC477359
0.7687	Intermediate Similarity	NPC310662
0.7687	Intermediate Similarity	NPC48929
0.7686	Intermediate Similarity	NPC186128
0.7686	Intermediate Similarity	NPC66208
0.7681	Intermediate Similarity	NPC42262
0.7681	Intermediate Similarity	NPC182869
0.7681	Intermediate Similarity	NPC327916
0.7681	Intermediate Similarity	NPC241349
0.7681	Intermediate Similarity	NPC472546
0.7681	Intermediate Similarity	NPC32749
0.7681	Intermediate Similarity	NPC147542
0.7681	Intermediate Similarity	NPC37992
0.7681	Intermediate Similarity	NPC220496
0.768	Intermediate Similarity	NPC254233
0.7672	Intermediate Similarity	NPC284477
0.7672	Intermediate Similarity	NPC25458
0.7672	Intermediate Similarity	NPC320891

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 NPC204784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	762
0.2-0.3	1345
0.3-0.4	2578
0.4-0.5	2436
0.5-0.6	1377
0.6-0.7	407
0.7-0.8	49
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD2182	Approved
0.819	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD5951	Approved
0.7845	Intermediate Similarity	NPD164	Approved
0.7833	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD2066	Phase 3
0.7786	Intermediate Similarity	NPD7008	Discontinued
0.777	Intermediate Similarity	NPD7236	Approved
0.7759	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1929	Approved
0.7759	Intermediate Similarity	NPD1930	Approved
0.775	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2067	Discontinued
0.7642	Intermediate Similarity	NPD2629	Approved
0.7642	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6287	Discontinued
0.7561	Intermediate Similarity	NPD6010	Discontinued
0.7542	Intermediate Similarity	NPD5909	Discontinued
0.7542	Intermediate Similarity	NPD1237	Approved
0.7537	Intermediate Similarity	NPD7961	Discontinued
0.7521	Intermediate Similarity	NPD1932	Approved
0.75	Intermediate Similarity	NPD1238	Approved
0.75	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7239	Suspended
0.75	Intermediate Similarity	NPD4879	Approved
0.75	Intermediate Similarity	NPD7609	Phase 3
0.7458	Intermediate Similarity	NPD6647	Phase 2
0.744	Intermediate Similarity	NPD4198	Discontinued
0.7434	Intermediate Similarity	NPD1088	Approved
0.7434	Intermediate Similarity	NPD7631	Approved
0.7391	Intermediate Similarity	NPD1989	Approved
0.7339	Intermediate Similarity	NPD6858	Approved
0.7339	Intermediate Similarity	NPD7094	Approved
0.7328	Intermediate Similarity	NPD3495	Discontinued
0.7304	Intermediate Similarity	NPD1693	Approved
0.7297	Intermediate Similarity	NPD650	Approved
0.7295	Intermediate Similarity	NPD2329	Discontinued
0.7293	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9545	Approved
0.7257	Intermediate Similarity	NPD1090	Approved
0.7257	Intermediate Similarity	NPD1086	Approved
0.7257	Intermediate Similarity	NPD1089	Approved
0.7254	Intermediate Similarity	NPD8166	Discontinued
0.7254	Intermediate Similarity	NPD4628	Phase 3
0.7252	Intermediate Similarity	NPD3972	Approved
0.7168	Intermediate Similarity	NPD800	Approved
0.7163	Intermediate Similarity	NPD2346	Discontinued
0.7155	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7058	Phase 2
0.7152	Intermediate Similarity	NPD7057	Phase 3
0.7133	Intermediate Similarity	NPD7003	Approved
0.7123	Intermediate Similarity	NPD6273	Approved
0.7121	Intermediate Similarity	NPD4878	Approved
0.7119	Intermediate Similarity	NPD9495	Approved
0.7105	Intermediate Similarity	NPD9258	Approved
0.7105	Intermediate Similarity	NPD9256	Approved
0.7097	Intermediate Similarity	NPD1317	Discontinued
0.708	Intermediate Similarity	NPD3764	Approved
0.7077	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1202	Approved
0.7063	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6599	Discontinued
0.7043	Intermediate Similarity	NPD1239	Approved
0.7042	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5305	Approved
0.7023	Intermediate Similarity	NPD5306	Approved
0.7021	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD7009	Phase 2
0.6992	Remote Similarity	NPD6637	Approved
0.6991	Remote Similarity	NPD1087	Approved
0.698	Remote Similarity	NPD7458	Discontinued
0.6978	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD9493	Approved
0.697	Remote Similarity	NPD4136	Approved
0.697	Remote Similarity	NPD4106	Approved
0.697	Remote Similarity	NPD4135	Approved
0.6957	Remote Similarity	NPD3672	Approved
0.6957	Remote Similarity	NPD2313	Discontinued
0.6957	Remote Similarity	NPD3673	Approved
0.6937	Remote Similarity	NPD9491	Approved
0.6923	Remote Similarity	NPD7610	Discontinued
0.6917	Remote Similarity	NPD4807	Approved
0.6917	Remote Similarity	NPD4806	Approved
0.6911	Remote Similarity	NPD5048	Discontinued
0.6906	Remote Similarity	NPD6663	Approved
0.6903	Remote Similarity	NPD9259	Approved
0.6903	Remote Similarity	NPD9257	Approved
0.6894	Remote Similarity	NPD2932	Approved
0.6891	Remote Similarity	NPD1564	Approved
0.6891	Remote Similarity	NPD1565	Approved
0.6891	Remote Similarity	NPD1566	Phase 3
0.6889	Remote Similarity	NPD1876	Approved
0.6889	Remote Similarity	NPD1283	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.6867	Remote Similarity	NPD3226	Approved
0.6861	Remote Similarity	NPD5736	Approved
0.6846	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1470	Approved
0.6835	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD4102	Approved
0.6818	Remote Similarity	NPD4105	Approved
0.6815	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6832	Phase 2
0.6806	Remote Similarity	NPD1471	Phase 3
0.6797	Remote Similarity	NPD2607	Approved
0.6797	Remote Similarity	NPD7819	Suspended
0.6788	Remote Similarity	NPD2798	Approved
0.6786	Remote Similarity	NPD7713	Phase 3
0.6783	Remote Similarity	NPD7305	Phase 1
0.6781	Remote Similarity	NPD3750	Approved
0.6767	Remote Similarity	NPD3019	Approved
0.6767	Remote Similarity	NPD2345	Approved
0.6761	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6799	Approved
0.6757	Remote Similarity	NPD3950	Discontinued
0.6755	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7799	Discontinued
0.6744	Remote Similarity	NPD2650	Approved
0.6744	Remote Similarity	NPD2652	Approved
0.6741	Remote Similarity	NPD9717	Approved
0.6738	Remote Similarity	NPD2979	Phase 3
0.6736	Remote Similarity	NPD2935	Discontinued
0.6735	Remote Similarity	NPD3887	Approved
0.6735	Remote Similarity	NPD2354	Approved
0.6724	Remote Similarity	NPD5346	Phase 2
0.6724	Remote Similarity	NPD5347	Phase 2
0.6723	Remote Similarity	NPD6049	Phase 2
0.6723	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD2797	Approved
0.6714	Remote Similarity	NPD6798	Discontinued
0.6696	Remote Similarity	NPD1282	Approved
0.6696	Remote Similarity	NPD4793	Discontinued
0.6694	Remote Similarity	NPD5926	Approved
0.6693	Remote Similarity	NPD4233	Approved
0.6693	Remote Similarity	NPD4234	Approved
0.6693	Remote Similarity	NPD1752	Approved
0.6693	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1756	Approved
0.6692	Remote Similarity	NPD4766	Approved
0.6692	Remote Similarity	NPD5691	Approved
0.669	Remote Similarity	NPD6355	Discontinued
0.6688	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2347	Approved
0.6667	Remote Similarity	NPD5277	Phase 2
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1201	Approved
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1778	Approved
0.6642	Remote Similarity	NPD2199	Approved
0.6642	Remote Similarity	NPD2198	Approved
0.6642	Remote Similarity	NPD5667	Approved
0.6642	Remote Similarity	NPD4626	Approved
0.6639	Remote Similarity	NPD1563	Approved
0.6637	Remote Similarity	NPD3971	Phase 1
0.6621	Remote Similarity	NPD5406	Approved
0.6621	Remote Similarity	NPD5408	Approved
0.6621	Remote Similarity	NPD5404	Approved
0.6621	Remote Similarity	NPD4476	Approved
0.6621	Remote Similarity	NPD5405	Approved
0.6621	Remote Similarity	NPD4477	Approved
0.6619	Remote Similarity	NPD5204	Approved
0.6618	Remote Similarity	NPD1608	Approved
0.6617	Remote Similarity	NPD1894	Discontinued
0.6613	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD226	Approved
0.66	Remote Similarity	NPD2532	Approved
0.66	Remote Similarity	NPD2534	Approved
0.66	Remote Similarity	NPD2533	Approved
0.6594	Remote Similarity	NPD3267	Approved
0.6594	Remote Similarity	NPD3266	Approved
0.6594	Remote Similarity	NPD1203	Approved
0.6593	Remote Similarity	NPD3026	Approved
0.6593	Remote Similarity	NPD3023	Approved
0.6589	Remote Similarity	NPD969	Suspended
0.6587	Remote Similarity	NPD6685	Approved
0.6587	Remote Similarity	NPD8434	Phase 2
0.6585	Remote Similarity	NPD8368	Discontinued
0.6577	Remote Similarity	NPD9490	Approved
0.6575	Remote Similarity	NPD2353	Approved
0.6575	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4617	Approved
0.6571	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4620	Approved
0.6571	Remote Similarity	NPD5203	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