NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.13
Volume:	293.34
LogP:	4.654
LogD:	3.796
LogS:	-6.399
# Rotatable Bonds:	1
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	3.081
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.056
MDCK Permeability:	1.737979255267419e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.428
30% Bioavailability (F30%):	0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	98.75875091552734%
Volume Distribution (VD):	1.003
Pgp-substrate:	1.2087571620941162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.839
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.706
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	1.518
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.769
Drug-inuced Liver Injury (DILI):	0.347
AMES Toxicity:	0.822
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.926
Carcinogencity:	0.889
Eye Corrosion:	0.005
Eye Irritation:	0.703
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC260233

Natural Product ID:	NPC260233
*Common Name:**	2-Isopropyl-8-Methyl-5,6-Dihydro-Phenanthrene-3,4-Dione
IUPAC Name:	8-methyl-2-propan-2-yl-5,6-dihydrophenanthrene-3,4-dione
Synonyms:
Standard InCHIKey:	VHACGKLOGFEKAM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O2/c1-10(2)15-9-12-7-8-13-11(3)5-4-6-14(13)16(12)18(20)17(15)19/h5,7-10H,4,6H2,1-3H3
SMILES:	CC(C)C1=Cc2ccc3C(=CCCc3c2C(=O)C1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL45023
PubChem CID:	14828180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	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
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1325	Protein Complex	GABA-A receptor; anion channel	Bos taurus	IC50	=	4400.0	nM	PMID[486398]

☑ 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 NPC260233 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	1572
0.2-0.3	4346
0.3-0.4	14402
0.4-0.5	14195
0.5-0.6	6583
0.6-0.7	1012
0.7-0.8	195
0.8-0.85	38
0.85-0.9	19
0.9-0.95	18
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC153885
0.967	High Similarity	NPC75724
0.9663	High Similarity	NPC238219
0.9659	High Similarity	NPC133461
0.956	High Similarity	NPC239185
0.9551	High Similarity	NPC155232
0.9457	High Similarity	NPC49994
0.9457	High Similarity	NPC134882
0.9348	High Similarity	NPC265220
0.9333	High Similarity	NPC188844
0.9333	High Similarity	NPC1682
0.9326	High Similarity	NPC173413
0.9255	High Similarity	NPC476993
0.9255	High Similarity	NPC109514
0.9239	High Similarity	NPC219573
0.9239	High Similarity	NPC185208
0.9222	High Similarity	NPC284475
0.9121	High Similarity	NPC323420
0.9101	High Similarity	NPC157778
0.9091	High Similarity	NPC307
0.9091	High Similarity	NPC160339
0.9022	High Similarity	NPC289883
0.8989	High Similarity	NPC43945
0.8913	High Similarity	NPC59677
0.8901	High Similarity	NPC277277
0.8866	High Similarity	NPC247976
0.8791	High Similarity	NPC418308
0.8778	High Similarity	NPC69057
0.8723	High Similarity	NPC472880
0.8696	High Similarity	NPC19256
0.8681	High Similarity	NPC267262
0.8614	High Similarity	NPC470252
0.86	High Similarity	NPC100767
0.8587	High Similarity	NPC298115
0.8539	High Similarity	NPC215008
0.8523	High Similarity	NPC145053
0.8478	Intermediate Similarity	NPC153308
0.8469	Intermediate Similarity	NPC472879
0.8462	Intermediate Similarity	NPC470253
0.8409	Intermediate Similarity	NPC285716
0.8409	Intermediate Similarity	NPC190567
0.8409	Intermediate Similarity	NPC17408
0.84	Intermediate Similarity	NPC329282
0.83	Intermediate Similarity	NPC474866
0.83	Intermediate Similarity	NPC471829
0.83	Intermediate Similarity	NPC475939
0.83	Intermediate Similarity	NPC472691
0.8295	Intermediate Similarity	NPC300205
0.8269	Intermediate Similarity	NPC265513
0.8261	Intermediate Similarity	NPC164526
0.8211	Intermediate Similarity	NPC103346
0.8208	Intermediate Similarity	NPC326664
0.8202	Intermediate Similarity	NPC164086
0.819	Intermediate Similarity	NPC292834
0.819	Intermediate Similarity	NPC280789
0.8182	Intermediate Similarity	NPC36342
0.8182	Intermediate Similarity	NPC103488
0.8182	Intermediate Similarity	NPC2785
0.8182	Intermediate Similarity	NPC285470
0.8152	Intermediate Similarity	NPC252067
0.8137	Intermediate Similarity	NPC172483
0.8137	Intermediate Similarity	NPC474910
0.8132	Intermediate Similarity	NPC273758
0.8113	Intermediate Similarity	NPC143768
0.8113	Intermediate Similarity	NPC93287
0.8111	Intermediate Similarity	NPC12936
0.8111	Intermediate Similarity	NPC273033
0.8095	Intermediate Similarity	NPC474057
0.8068	Intermediate Similarity	NPC245966
0.8058	Intermediate Similarity	NPC472699
0.8058	Intermediate Similarity	NPC472700
0.8037	Intermediate Similarity	NPC471721
0.8021	Intermediate Similarity	NPC125226
0.8	Intermediate Similarity	NPC325709
0.8	Intermediate Similarity	NPC71664
0.8	Intermediate Similarity	NPC113307
0.7982	Intermediate Similarity	NPC469843
0.7981	Intermediate Similarity	NPC472695
0.7981	Intermediate Similarity	NPC472701
0.7981	Intermediate Similarity	NPC472683
0.7981	Intermediate Similarity	NPC472696
0.7963	Intermediate Similarity	NPC474095
0.7963	Intermediate Similarity	NPC215419
0.7941	Intermediate Similarity	NPC274443
0.7935	Intermediate Similarity	NPC39600
0.7935	Intermediate Similarity	NPC197581
0.7917	Intermediate Similarity	NPC303967
0.7917	Intermediate Similarity	NPC67585
0.7917	Intermediate Similarity	NPC110420
0.7889	Intermediate Similarity	NPC139901
0.7889	Intermediate Similarity	NPC151405
0.787	Intermediate Similarity	NPC67377
0.785	Intermediate Similarity	NPC218855
0.785	Intermediate Similarity	NPC186128
0.7843	Intermediate Similarity	NPC244427
0.7843	Intermediate Similarity	NPC222390
0.7838	Intermediate Similarity	NPC318173
0.781	Intermediate Similarity	NPC203732
0.7798	Intermediate Similarity	NPC217111
0.7798	Intermediate Similarity	NPC228936
0.7788	Intermediate Similarity	NPC134120
0.7778	Intermediate Similarity	NPC471481
0.7767	Intermediate Similarity	NPC329556
0.7748	Intermediate Similarity	NPC80605
0.7748	Intermediate Similarity	NPC222968
0.7748	Intermediate Similarity	NPC323440
0.7736	Intermediate Similarity	NPC192577
0.7732	Intermediate Similarity	NPC26224
0.7732	Intermediate Similarity	NPC58872
0.7717	Intermediate Similarity	NPC100039
0.7717	Intermediate Similarity	NPC73978
0.7714	Intermediate Similarity	NPC83409
0.7714	Intermediate Similarity	NPC185763
0.7714	Intermediate Similarity	NPC37914
0.7706	Intermediate Similarity	NPC130591
0.7706	Intermediate Similarity	NPC234637
0.7699	Intermediate Similarity	NPC232958
0.7692	Intermediate Similarity	NPC272260
0.7667	Intermediate Similarity	NPC9796
0.7647	Intermediate Similarity	NPC221825
0.7636	Intermediate Similarity	NPC93181
0.7624	Intermediate Similarity	NPC240042
0.7624	Intermediate Similarity	NPC226041
0.7619	Intermediate Similarity	NPC471186
0.7615	Intermediate Similarity	NPC13784
0.7614	Intermediate Similarity	NPC285679
0.7611	Intermediate Similarity	NPC202015
0.7609	Intermediate Similarity	NPC157055
0.7609	Intermediate Similarity	NPC477703
0.7609	Intermediate Similarity	NPC95868
0.7593	Intermediate Similarity	NPC137315
0.7573	Intermediate Similarity	NPC136810
0.7573	Intermediate Similarity	NPC225079
0.7573	Intermediate Similarity	NPC112552
0.7573	Intermediate Similarity	NPC133809
0.7573	Intermediate Similarity	NPC128248
0.7568	Intermediate Similarity	NPC135730
0.7568	Intermediate Similarity	NPC260886
0.7549	Intermediate Similarity	NPC145052
0.7523	Intermediate Similarity	NPC66208
0.75	Intermediate Similarity	NPC74458
0.7478	Intermediate Similarity	NPC472981
0.7478	Intermediate Similarity	NPC144547
0.7477	Intermediate Similarity	NPC112903
0.7477	Intermediate Similarity	NPC186933
0.7475	Intermediate Similarity	NPC475059
0.7475	Intermediate Similarity	NPC475023
0.7474	Intermediate Similarity	NPC267704
0.7473	Intermediate Similarity	NPC179726
0.7456	Intermediate Similarity	NPC476645
0.7451	Intermediate Similarity	NPC156021
0.7447	Intermediate Similarity	NPC230068
0.7436	Intermediate Similarity	NPC318067
0.7436	Intermediate Similarity	NPC328107
0.7434	Intermediate Similarity	NPC61651
0.7434	Intermediate Similarity	NPC268930
0.7431	Intermediate Similarity	NPC291799
0.7416	Intermediate Similarity	NPC54269
0.7414	Intermediate Similarity	NPC167323
0.7414	Intermediate Similarity	NPC269923
0.74	Intermediate Similarity	NPC475057
0.7396	Intermediate Similarity	NPC123476
0.7391	Intermediate Similarity	NPC238861
0.7391	Intermediate Similarity	NPC137847
0.7391	Intermediate Similarity	NPC988
0.7391	Intermediate Similarity	NPC77000
0.7391	Intermediate Similarity	NPC76455
0.7391	Intermediate Similarity	NPC289432
0.7387	Intermediate Similarity	NPC196673
0.7386	Intermediate Similarity	NPC95289
0.7368	Intermediate Similarity	NPC149263
0.7368	Intermediate Similarity	NPC324624
0.7364	Intermediate Similarity	NPC212415
0.7353	Intermediate Similarity	NPC12695
0.7347	Intermediate Similarity	NPC477704
0.7347	Intermediate Similarity	NPC477693
0.734	Intermediate Similarity	NPC242628
0.7321	Intermediate Similarity	NPC274839
0.7315	Intermediate Similarity	NPC470007
0.7308	Intermediate Similarity	NPC476042
0.729	Intermediate Similarity	NPC167336
0.7288	Intermediate Similarity	NPC85511
0.7283	Intermediate Similarity	NPC298023
0.7283	Intermediate Similarity	NPC329318
0.7283	Intermediate Similarity	NPC3190
0.7283	Intermediate Similarity	NPC249018
0.7282	Intermediate Similarity	NPC103048
0.7273	Intermediate Similarity	NPC98880
0.7273	Intermediate Similarity	NPC210089
0.7248	Intermediate Similarity	NPC318327
0.7241	Intermediate Similarity	NPC476225
0.7232	Intermediate Similarity	NPC196075
0.7232	Intermediate Similarity	NPC241851
0.7222	Intermediate Similarity	NPC142326
0.7222	Intermediate Similarity	NPC94751
0.7217	Intermediate Similarity	NPC472697
0.7217	Intermediate Similarity	NPC472698
0.7212	Intermediate Similarity	NPC329387
0.7212	Intermediate Similarity	NPC317280
0.7207	Intermediate Similarity	NPC471188

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 NPC260233 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	1037
0.2-0.3	1454
0.3-0.4	3271
0.4-0.5	2139
0.5-0.6	790
0.6-0.7	131
0.7-0.8	35
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.956	High Similarity	NPD3495	Discontinued
0.9333	High Similarity	NPD7631	Approved
0.9222	High Similarity	NPD7609	Phase 3
0.8989	High Similarity	NPD650	Approved
0.8269	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1508	Approved
0.8111	Intermediate Similarity	NPD942	Approved
0.7879	Intermediate Similarity	NPD1843	Approved
0.7822	Intermediate Similarity	NPD2066	Phase 3
0.7767	Intermediate Similarity	NPD1930	Approved
0.7767	Intermediate Similarity	NPD1929	Approved
0.7767	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7009	Phase 2
0.7677	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2193	Phase 2
0.767	Intermediate Similarity	NPD2648	Phase 3
0.7609	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1932	Approved
0.75	Intermediate Similarity	NPD2196	Discontinued
0.7478	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5951	Approved
0.7434	Intermediate Similarity	NPD7610	Discontinued
0.7423	Intermediate Similarity	NPD1087	Approved
0.7423	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2329	Discontinued
0.7391	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5836	Discontinued
0.7364	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6049	Phase 2
0.7255	Intermediate Similarity	NPD1693	Approved
0.7248	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1090	Approved
0.72	Intermediate Similarity	NPD1086	Approved
0.72	Intermediate Similarity	NPD1089	Approved
0.7179	Intermediate Similarity	NPD4879	Approved
0.717	Intermediate Similarity	NPD2171	Approved
0.7143	Intermediate Similarity	NPD7094	Approved
0.7143	Intermediate Similarity	NPD6858	Approved
0.713	Intermediate Similarity	NPD2192	Approved
0.713	Intermediate Similarity	NPD1677	Discontinued
0.713	Intermediate Similarity	NPD2197	Approved
0.71	Intermediate Similarity	NPD800	Approved
0.7059	Intermediate Similarity	NPD1088	Approved
0.7037	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1317	Discontinued
0.7019	Intermediate Similarity	NPD1989	Approved
0.701	Intermediate Similarity	NPD3971	Phase 1
0.699	Remote Similarity	NPD1563	Approved
0.6964	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3317	Approved
0.6952	Remote Similarity	NPD1099	Approved
0.6952	Remote Similarity	NPD1100	Approved
0.6944	Remote Similarity	NPD3357	Discontinued
0.6923	Remote Similarity	NPD4094	Approved
0.6923	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4878	Approved
0.6881	Remote Similarity	NPD5909	Discontinued
0.6875	Remote Similarity	NPD664	Approved
0.6869	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3672	Approved
0.6863	Remote Similarity	NPD3673	Approved
0.6803	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2754	Discontinued
0.6796	Remote Similarity	NPD1239	Approved
0.6792	Remote Similarity	NPD4657	Approved
0.6792	Remote Similarity	NPD1566	Phase 3
0.6792	Remote Similarity	NPD4655	Approved
0.6792	Remote Similarity	NPD1564	Approved
0.6792	Remote Similarity	NPD1565	Approved
0.6786	Remote Similarity	NPD2182	Approved
0.6765	Remote Similarity	NPD5347	Phase 2
0.6765	Remote Similarity	NPD5346	Phase 2
0.675	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1237	Approved
0.6727	Remote Similarity	NPD164	Approved
0.6697	Remote Similarity	NPD6024	Approved
0.6697	Remote Similarity	NPD813	Approved
0.6697	Remote Similarity	NPD6027	Approved
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1202	Approved
0.6667	Remote Similarity	NPD2345	Approved
0.6638	Remote Similarity	NPD7077	Approved
0.6638	Remote Similarity	NPD7076	Approved
0.6634	Remote Similarity	NPD9259	Approved
0.6634	Remote Similarity	NPD9257	Approved
0.6613	Remote Similarity	NPD3244	Pre-registration
0.6613	Remote Similarity	NPD3245	Phase 3
0.6598	Remote Similarity	NPD9490	Approved
0.6596	Remote Similarity	NPD4687	Approved
0.6596	Remote Similarity	NPD4058	Approved
0.6581	Remote Similarity	NPD2508	Discontinued
0.6569	Remote Similarity	NPD4793	Discontinued
0.6562	Remote Similarity	NPD7961	Discontinued
0.6529	Remote Similarity	NPD2932	Approved
0.6508	Remote Similarity	NPD7084	Phase 3
0.6504	Remote Similarity	NPD3972	Approved
0.65	Remote Similarity	NPD9491	Approved
0.6486	Remote Similarity	NPD6647	Phase 2
0.6465	Remote Similarity	NPD226	Approved
0.6455	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3547	Approved
0.6452	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3549	Approved
0.6446	Remote Similarity	NPD3025	Approved
0.6446	Remote Similarity	NPD3024	Approved
0.6446	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1245	Approved
0.6441	Remote Similarity	NPD2319	Discontinued
0.6423	Remote Similarity	NPD6287	Discontinued
0.6423	Remote Similarity	NPD1201	Approved
0.6421	Remote Similarity	NPD5733	Approved
0.6417	Remote Similarity	NPD997	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1876	Approved
0.6393	Remote Similarity	NPD3019	Approved
0.6383	Remote Similarity	NPD5276	Approved
0.6381	Remote Similarity	NPD9258	Approved
0.6381	Remote Similarity	NPD9256	Approved
0.6364	Remote Similarity	NPD1238	Approved
0.6356	Remote Similarity	NPD6010	Discontinued
0.6354	Remote Similarity	NPD9716	Approved
0.6349	Remote Similarity	NPD1470	Approved
0.6341	Remote Similarity	NPD3023	Approved
0.6341	Remote Similarity	NPD3026	Approved
0.6333	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7055	Discontinued
0.632	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3099	Discontinued
0.6311	Remote Similarity	NPD1651	Approved
0.6308	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1246	Approved
0.6299	Remote Similarity	NPD2798	Approved
0.6299	Remote Similarity	NPD4980	Approved
0.6281	Remote Similarity	NPD6065	Approved
0.6277	Remote Similarity	NPD4691	Approved
0.6275	Remote Similarity	NPD4544	Approved
0.6273	Remote Similarity	NPD466	Approved
0.627	Remote Similarity	NPD2056	Discontinued
0.626	Remote Similarity	NPD4199	Phase 3
0.625	Remote Similarity	NPD4803	Discontinued
0.624	Remote Similarity	NPD3356	Approved
0.624	Remote Similarity	NPD3355	Approved
0.6231	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD2346	Discontinued
0.622	Remote Similarity	NPD5653	Discontinued
0.6216	Remote Similarity	NPD7798	Approved
0.6204	Remote Similarity	NPD7003	Approved
0.6195	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5157	Phase 1
0.619	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5159	Phase 2
0.6183	Remote Similarity	NPD7713	Phase 3
0.6176	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.617	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4137	Phase 3
0.6168	Remote Similarity	NPD1007	Discontinued
0.616	Remote Similarity	NPD1281	Approved
0.6159	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD675	Discontinued
0.6154	Remote Similarity	NPD6966	Discovery
0.6148	Remote Similarity	NPD5408	Approved
0.6148	Remote Similarity	NPD5404	Approved
0.6148	Remote Similarity	NPD5406	Approved
0.6148	Remote Similarity	NPD5405	Approved
0.6147	Remote Similarity	NPD9260	Approved
0.6142	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4733	Approved
0.6126	Remote Similarity	NPD5926	Approved
0.6111	Remote Similarity	NPD6637	Approved
0.6107	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4747	Approved
0.6102	Remote Similarity	NPD3644	Approved
0.6102	Remote Similarity	NPD3643	Approved
0.6102	Remote Similarity	NPD3642	Approved
0.6091	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD2895	Discontinued
0.6091	Remote Similarity	NPD3093	Approved
0.6083	Remote Similarity	NPD1241	Discontinued
0.6074	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD742	Approved
0.6066	Remote Similarity	NPD4574	Approved
0.6066	Remote Similarity	NPD4576	Approved
0.6048	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3979	Approved
0.604	Remote Similarity	NPD3903	Approved
0.604	Remote Similarity	NPD3981	Approved
0.604	Remote Similarity	NPD3904	Approved
0.6038	Remote Similarity	NPD1101	Approved
0.6033	Remote Similarity	NPD1075	Approved
0.6033	Remote Similarity	NPD1074	Approved
0.6033	Remote Similarity	NPD2629	Approved
0.6033	Remote Similarity	NPD1073	Approved
0.6033	Remote Similarity	NPD4766	Approved
0.6033	Remote Similarity	NPD690	Clinical (unspecified phase)

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