NPASS Compound

Structure

NPC238219 OpenBabel07101718282D 22 23 0 0 0 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 -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 1.7321 2.0000 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 0.8660 1.5000 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 0.8660 -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 2.5981 3.5000 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 1.7321 0.0000 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 -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 -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 -0.8660 -1.5000 0.0000 C 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 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 15 19 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 2 0 0 0 0 20 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.18
Volume:	336.488
LogP:	6.559
LogD:	4.314
LogS:	-3.95
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	2.923
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	1.6601219613221474e-05
Pgp-inhibitor:	0.848
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	98.15666198730469%
Volume Distribution (VD):	2.268
Pgp-substrate:	2.5936028957366943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.718
CYP2D6-substrate:	0.836
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	10.951
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.528
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.651
Skin Sensitization:	0.945
Carcinogencity:	0.204
Eye Corrosion:	0.008
Eye Irritation:	0.935
Respiratory Toxicity:	0.725

Download Data

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

Natural Product: NPC238219

Natural Product ID:	NPC238219
*Common Name:**	Sahandinone
IUPAC Name:	6-methyl-5-(4-methylpent-3-enyl)-2-propan-2-ylnaphthalene-1,4-dione
Synonyms:	Sahandinone
Standard InCHIKey:	HDPJWDKSOMAYFT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H24O2/c1-12(2)7-6-8-15-14(5)9-10-16-19(15)18(21)11-17(13(3)4)20(16)22/h7,9-11,13H,6,8H2,1-5H3
SMILES:	CC(=CCCc1c(C)ccc2c1C(=O)C=C(C2=O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813351
PubChem CID:	56666274
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
NPO18542	Salvia sahendica	Species	Lamiaceae	Eukaryota	n.a.	collected from the plants natural habitat in Tabriz, Northwestern Iran, at an altitude of 1400 m	n.a.	PMID[21775156]
NPO18542	Salvia sahendica	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	10180.0	nM	PMID[473241]

☑ 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 NPC238219 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	306
0.1-0.2	1603
0.2-0.3	4716
0.3-0.4	14762
0.4-0.5	13941
0.5-0.6	6139
0.6-0.7	956
0.7-0.8	188
0.8-0.85	40
0.85-0.9	16
0.9-0.95	19
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC155232
0.9885	High Similarity	NPC153885
0.977	High Similarity	NPC133461
0.9663	High Similarity	NPC260233
0.9659	High Similarity	NPC1682
0.9659	High Similarity	NPC188844
0.9655	High Similarity	NPC173413
0.956	High Similarity	NPC49994
0.956	High Similarity	NPC134882
0.956	High Similarity	NPC75724
0.9545	High Similarity	NPC284475
0.9451	High Similarity	NPC239185
0.9451	High Similarity	NPC265220
0.9425	High Similarity	NPC157778
0.9355	High Similarity	NPC109514
0.9355	High Similarity	NPC476993
0.931	High Similarity	NPC43945
0.9222	High Similarity	NPC323420
0.9222	High Similarity	NPC59677
0.9195	High Similarity	NPC307
0.9195	High Similarity	NPC160339
0.913	High Similarity	NPC219573
0.913	High Similarity	NPC185208
0.9121	High Similarity	NPC289883
0.9	High Similarity	NPC277277
0.8958	High Similarity	NPC247976
0.8876	High Similarity	NPC69057
0.8851	High Similarity	NPC215008
0.8791	High Similarity	NPC19256
0.87	High Similarity	NPC470252
0.8687	High Similarity	NPC100767
0.8681	High Similarity	NPC418308
0.8673	High Similarity	NPC329282
0.8621	High Similarity	NPC145053
0.8617	High Similarity	NPC472880
0.8571	High Similarity	NPC153308
0.8571	High Similarity	NPC267262
0.8506	High Similarity	NPC190567
0.8506	High Similarity	NPC17408
0.8506	High Similarity	NPC285716
0.8478	Intermediate Similarity	NPC298115
0.8447	Intermediate Similarity	NPC292834
0.84	Intermediate Similarity	NPC172483
0.84	Intermediate Similarity	NPC474910
0.8391	Intermediate Similarity	NPC300205
0.8367	Intermediate Similarity	NPC472879
0.8365	Intermediate Similarity	NPC470253
0.8352	Intermediate Similarity	NPC164526
0.8298	Intermediate Similarity	NPC103346
0.8295	Intermediate Similarity	NPC164086
0.8286	Intermediate Similarity	NPC326664
0.8276	Intermediate Similarity	NPC36342
0.8276	Intermediate Similarity	NPC285470
0.8276	Intermediate Similarity	NPC2785
0.8276	Intermediate Similarity	NPC103488
0.8242	Intermediate Similarity	NPC252067
0.8222	Intermediate Similarity	NPC273758
0.8202	Intermediate Similarity	NPC12936
0.8202	Intermediate Similarity	NPC273033
0.82	Intermediate Similarity	NPC471829
0.82	Intermediate Similarity	NPC475939
0.82	Intermediate Similarity	NPC474866
0.82	Intermediate Similarity	NPC472691
0.82	Intermediate Similarity	NPC274443
0.819	Intermediate Similarity	NPC143768
0.8173	Intermediate Similarity	NPC265513
0.8173	Intermediate Similarity	NPC474057
0.8161	Intermediate Similarity	NPC245966
0.81	Intermediate Similarity	NPC244427
0.81	Intermediate Similarity	NPC222390
0.8095	Intermediate Similarity	NPC280789
0.809	Intermediate Similarity	NPC71664
0.8085	Intermediate Similarity	NPC325709
0.8085	Intermediate Similarity	NPC113307
0.8037	Intermediate Similarity	NPC217111
0.8022	Intermediate Similarity	NPC39600
0.8022	Intermediate Similarity	NPC197581
0.8019	Intermediate Similarity	NPC93287
0.8	Intermediate Similarity	NPC110420
0.8	Intermediate Similarity	NPC67585
0.8	Intermediate Similarity	NPC303967
0.7978	Intermediate Similarity	NPC139901
0.7978	Intermediate Similarity	NPC151405
0.7961	Intermediate Similarity	NPC472699
0.7961	Intermediate Similarity	NPC472700
0.7944	Intermediate Similarity	NPC471721
0.7917	Intermediate Similarity	NPC125226
0.7909	Intermediate Similarity	NPC318173
0.789	Intermediate Similarity	NPC469843
0.7885	Intermediate Similarity	NPC472701
0.7885	Intermediate Similarity	NPC472683
0.7885	Intermediate Similarity	NPC472696
0.7885	Intermediate Similarity	NPC472695
0.787	Intermediate Similarity	NPC474095
0.787	Intermediate Similarity	NPC215419
0.7843	Intermediate Similarity	NPC329556
0.7822	Intermediate Similarity	NPC112552
0.7818	Intermediate Similarity	NPC80605
0.7818	Intermediate Similarity	NPC323440
0.7818	Intermediate Similarity	NPC222968
0.7812	Intermediate Similarity	NPC26224
0.7812	Intermediate Similarity	NPC58872
0.781	Intermediate Similarity	NPC192577
0.7802	Intermediate Similarity	NPC73978
0.7802	Intermediate Similarity	NPC100039
0.7788	Intermediate Similarity	NPC185763
0.7788	Intermediate Similarity	NPC37914
0.7788	Intermediate Similarity	NPC83409
0.7778	Intermediate Similarity	NPC272260
0.7778	Intermediate Similarity	NPC67377
0.7757	Intermediate Similarity	NPC186128
0.7757	Intermediate Similarity	NPC218855
0.7753	Intermediate Similarity	NPC9796
0.7714	Intermediate Similarity	NPC203732
0.7706	Intermediate Similarity	NPC228936
0.7706	Intermediate Similarity	NPC93181
0.7701	Intermediate Similarity	NPC285679
0.77	Intermediate Similarity	NPC156021
0.77	Intermediate Similarity	NPC240042
0.77	Intermediate Similarity	NPC226041
0.7692	Intermediate Similarity	NPC477703
0.7692	Intermediate Similarity	NPC95868
0.7692	Intermediate Similarity	NPC157055
0.7692	Intermediate Similarity	NPC134120
0.7685	Intermediate Similarity	NPC471481
0.7679	Intermediate Similarity	NPC202015
0.7664	Intermediate Similarity	NPC137315
0.7647	Intermediate Similarity	NPC225079
0.7624	Intermediate Similarity	NPC145052
0.7615	Intermediate Similarity	NPC234637
0.7615	Intermediate Similarity	NPC130591
0.7611	Intermediate Similarity	NPC232958
0.7593	Intermediate Similarity	NPC66208
0.7586	Intermediate Similarity	NPC74458
0.7556	Intermediate Similarity	NPC179726
0.7553	Intermediate Similarity	NPC267704
0.7551	Intermediate Similarity	NPC475023
0.7551	Intermediate Similarity	NPC475059
0.7549	Intermediate Similarity	NPC221825
0.7547	Intermediate Similarity	NPC112903
0.7545	Intermediate Similarity	NPC186933
0.7527	Intermediate Similarity	NPC230068
0.7524	Intermediate Similarity	NPC471186
0.7523	Intermediate Similarity	NPC13784
0.75	Intermediate Similarity	NPC318067
0.75	Intermediate Similarity	NPC291799
0.75	Intermediate Similarity	NPC54269
0.75	Intermediate Similarity	NPC328107
0.7477	Intermediate Similarity	NPC260886
0.7477	Intermediate Similarity	NPC135730
0.7476	Intermediate Similarity	NPC133809
0.7476	Intermediate Similarity	NPC128248
0.7476	Intermediate Similarity	NPC136810
0.7475	Intermediate Similarity	NPC475057
0.7474	Intermediate Similarity	NPC123476
0.7473	Intermediate Similarity	NPC137847
0.7473	Intermediate Similarity	NPC76455
0.7471	Intermediate Similarity	NPC95289
0.7455	Intermediate Similarity	NPC196673
0.7455	Intermediate Similarity	NPC241851
0.7447	Intermediate Similarity	NPC149263
0.7447	Intermediate Similarity	NPC324624
0.7423	Intermediate Similarity	NPC477704
0.7423	Intermediate Similarity	NPC477693
0.7419	Intermediate Similarity	NPC242628
0.7391	Intermediate Similarity	NPC472981
0.7391	Intermediate Similarity	NPC144547
0.7387	Intermediate Similarity	NPC470764
0.7387	Intermediate Similarity	NPC274839
0.7383	Intermediate Similarity	NPC470391
0.7368	Intermediate Similarity	NPC204784
0.7368	Intermediate Similarity	NPC476645
0.7363	Intermediate Similarity	NPC298023
0.7363	Intermediate Similarity	NPC329318
0.7356	Intermediate Similarity	NPC98880
0.7345	Intermediate Similarity	NPC61651
0.7345	Intermediate Similarity	NPC268930
0.7339	Intermediate Similarity	NPC210089
0.7328	Intermediate Similarity	NPC167323
0.7328	Intermediate Similarity	NPC269923
0.7315	Intermediate Similarity	NPC318327
0.7304	Intermediate Similarity	NPC289432
0.7304	Intermediate Similarity	NPC238861
0.7304	Intermediate Similarity	NPC77000
0.7304	Intermediate Similarity	NPC988
0.7282	Intermediate Similarity	NPC317280
0.7282	Intermediate Similarity	NPC329387
0.7273	Intermediate Similarity	NPC86670
0.7273	Intermediate Similarity	NPC274455
0.7273	Intermediate Similarity	NPC212415
0.7273	Intermediate Similarity	NPC70940
0.7257	Intermediate Similarity	NPC158157
0.7255	Intermediate Similarity	NPC12695
0.7253	Intermediate Similarity	NPC78500
0.7245	Intermediate Similarity	NPC473345
0.7241	Intermediate Similarity	NPC311343
0.7238	Intermediate Similarity	NPC25458
0.7238	Intermediate Similarity	NPC304873
0.7232	Intermediate Similarity	NPC476357
0.7222	Intermediate Similarity	NPC470007

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 NPC238219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	1040
0.2-0.3	1541
0.3-0.4	3300
0.4-0.5	2083
0.5-0.6	735
0.6-0.7	124
0.7-0.8	34
0.8-0.85	3
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9659	High Similarity	NPD7631	Approved
0.9545	High Similarity	NPD7609	Phase 3
0.9451	High Similarity	NPD3495	Discontinued
0.931	High Similarity	NPD650	Approved
0.8404	Intermediate Similarity	NPD1508	Approved
0.835	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD942	Approved
0.8144	Intermediate Similarity	NPD1843	Approved
0.79	Intermediate Similarity	NPD2066	Phase 3
0.7843	Intermediate Similarity	NPD1929	Approved
0.7843	Intermediate Similarity	NPD1930	Approved
0.7843	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD1932	Approved
0.7745	Intermediate Similarity	NPD2193	Phase 2
0.7745	Intermediate Similarity	NPD2648	Phase 3
0.7692	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD2329	Discontinued
0.7573	Intermediate Similarity	NPD2196	Discontinued
0.75	Intermediate Similarity	NPD1087	Approved
0.75	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7009	Phase 2
0.7387	Intermediate Similarity	NPD5951	Approved
0.7345	Intermediate Similarity	NPD7610	Discontinued
0.7327	Intermediate Similarity	NPD6049	Phase 2
0.7327	Intermediate Similarity	NPD1693	Approved
0.7327	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5836	Discontinued
0.7273	Intermediate Similarity	NPD1090	Approved
0.7273	Intermediate Similarity	NPD1086	Approved
0.7273	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1089	Approved
0.7248	Intermediate Similarity	NPD1317	Discontinued
0.7241	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4879	Approved
0.7238	Intermediate Similarity	NPD2171	Approved
0.7196	Intermediate Similarity	NPD2192	Approved
0.7196	Intermediate Similarity	NPD1677	Discontinued
0.7196	Intermediate Similarity	NPD2197	Approved
0.7172	Intermediate Similarity	NPD800	Approved
0.7155	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD1088	Approved
0.7103	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1989	Approved
0.7083	Intermediate Similarity	NPD3971	Phase 1
0.7059	Intermediate Similarity	NPD1563	Approved
0.7054	Intermediate Similarity	NPD6858	Approved
0.7054	Intermediate Similarity	NPD7094	Approved
0.7027	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1099	Approved
0.7019	Intermediate Similarity	NPD1100	Approved
0.7009	Intermediate Similarity	NPD3357	Discontinued
0.7	Intermediate Similarity	NPD2182	Approved
0.699	Remote Similarity	NPD4094	Approved
0.699	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD164	Approved
0.6939	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD664	Approved
0.6931	Remote Similarity	NPD3673	Approved
0.6931	Remote Similarity	NPD3672	Approved
0.687	Remote Similarity	NPD3317	Approved
0.6863	Remote Similarity	NPD1239	Approved
0.6857	Remote Similarity	NPD1565	Approved
0.6857	Remote Similarity	NPD1566	Phase 3
0.6857	Remote Similarity	NPD1564	Approved
0.6857	Remote Similarity	NPD4655	Approved
0.6857	Remote Similarity	NPD4657	Approved
0.6833	Remote Similarity	NPD4878	Approved
0.6832	Remote Similarity	NPD5346	Phase 2
0.6832	Remote Similarity	NPD5347	Phase 2
0.6789	Remote Similarity	NPD1237	Approved
0.6789	Remote Similarity	NPD5909	Discontinued
0.6759	Remote Similarity	NPD813	Approved
0.6737	Remote Similarity	NPD225	Approved
0.6737	Remote Similarity	NPD227	Approved
0.6731	Remote Similarity	NPD1202	Approved
0.6723	Remote Similarity	NPD2345	Approved
0.6721	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2754	Discontinued
0.67	Remote Similarity	NPD9259	Approved
0.67	Remote Similarity	NPD9257	Approved
0.6696	Remote Similarity	NPD7076	Approved
0.6696	Remote Similarity	NPD7077	Approved
0.6667	Remote Similarity	NPD9490	Approved
0.6667	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4793	Discontinued
0.6614	Remote Similarity	NPD7961	Discontinued
0.6606	Remote Similarity	NPD6024	Approved
0.6606	Remote Similarity	NPD6027	Approved
0.6587	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7008	Discontinued
0.6585	Remote Similarity	NPD1876	Approved
0.6566	Remote Similarity	NPD9491	Approved
0.6557	Remote Similarity	NPD3972	Approved
0.6545	Remote Similarity	NPD6647	Phase 2
0.6532	Remote Similarity	NPD3244	Pre-registration
0.6532	Remote Similarity	NPD3245	Phase 3
0.6531	Remote Similarity	NPD226	Approved
0.6525	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1245	Approved
0.65	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD2508	Discontinued
0.6489	Remote Similarity	NPD4058	Approved
0.6481	Remote Similarity	NPD466	Approved
0.6475	Remote Similarity	NPD6287	Discontinued
0.6471	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2932	Approved
0.6442	Remote Similarity	NPD9256	Approved
0.6442	Remote Similarity	NPD9258	Approved
0.6422	Remote Similarity	NPD1238	Approved
0.6421	Remote Similarity	NPD9716	Approved
0.64	Remote Similarity	NPD1470	Approved
0.6373	Remote Similarity	NPD3099	Discontinued
0.6371	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3549	Approved
0.6371	Remote Similarity	NPD3547	Approved
0.6371	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1651	Approved
0.6364	Remote Similarity	NPD3024	Approved
0.6364	Remote Similarity	NPD3025	Approved
0.6357	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD1246	Approved
0.6356	Remote Similarity	NPD2319	Discontinued
0.6341	Remote Similarity	NPD1201	Approved
0.6333	Remote Similarity	NPD6065	Approved
0.632	Remote Similarity	NPD2056	Discontinued
0.6316	Remote Similarity	NPD4687	Approved
0.6311	Remote Similarity	NPD3019	Approved
0.6306	Remote Similarity	NPD4803	Discontinued
0.6299	Remote Similarity	NPD7084	Phase 3
0.629	Remote Similarity	NPD3356	Approved
0.629	Remote Similarity	NPD3355	Approved
0.6279	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD742	Approved
0.6271	Remote Similarity	NPD6010	Discontinued
0.626	Remote Similarity	NPD3023	Approved
0.626	Remote Similarity	NPD3026	Approved
0.625	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1007	Discontinued
0.6222	Remote Similarity	NPD675	Discontinued
0.622	Remote Similarity	NPD4980	Approved
0.622	Remote Similarity	NPD2798	Approved
0.622	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.621	Remote Similarity	NPD1281	Approved
0.6204	Remote Similarity	NPD9260	Approved
0.6204	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5926	Approved
0.6179	Remote Similarity	NPD4199	Phase 3
0.6176	Remote Similarity	NPD4544	Approved
0.617	Remote Similarity	NPD4691	Approved
0.616	Remote Similarity	NPD6637	Approved
0.6154	Remote Similarity	NPD3644	Approved
0.6154	Remote Similarity	NPD3642	Approved
0.6154	Remote Similarity	NPD3643	Approved
0.6148	Remote Similarity	NPD2346	Discontinued
0.6147	Remote Similarity	NPD3093	Approved
0.6147	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5733	Approved
0.6142	Remote Similarity	NPD5653	Discontinued
0.6134	Remote Similarity	NPD1241	Discontinued
0.6131	Remote Similarity	NPD7003	Approved
0.6126	Remote Similarity	NPD7798	Approved
0.6124	Remote Similarity	NPD7055	Discontinued
0.6119	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5157	Phase 1
0.6111	Remote Similarity	NPD5159	Phase 2
0.6111	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7713	Phase 3
0.6105	Remote Similarity	NPD5276	Approved
0.61	Remote Similarity	NPD3981	Approved
0.61	Remote Similarity	NPD3903	Approved
0.61	Remote Similarity	NPD3904	Approved
0.61	Remote Similarity	NPD3979	Approved
0.6098	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1101	Approved
0.6083	Remote Similarity	NPD2629	Approved
0.6083	Remote Similarity	NPD4766	Approved
0.6083	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD1074	Approved
0.6083	Remote Similarity	NPD1073	Approved
0.6083	Remote Similarity	NPD1075	Approved
0.6078	Remote Similarity	NPD4635	Approved
0.6077	Remote Similarity	NPD6966	Discovery
0.6074	Remote Similarity	NPD5406	Approved
0.6074	Remote Similarity	NPD5404	Approved
0.6074	Remote Similarity	NPD5408	Approved
0.6074	Remote Similarity	NPD5405	Approved
0.6071	Remote Similarity	NPD5630	Phase 1
0.6068	Remote Similarity	NPD2067	Discontinued
0.6064	Remote Similarity	NPD4137	Phase 3
0.6063	Remote Similarity	NPD1283	Approved
0.6063	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5277	Phase 2
0.605	Remote Similarity	NPD2607	Approved
0.6048	Remote Similarity	NPD4733	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