NPASS Compound

Structure

NPC472699 OpenBabel07101718232D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.0162 -1.7121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0012 -3.0240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6881 1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8750 1.9553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9051 1.5676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1158 0.6442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2897 0.9165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2809 -0.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4739 1.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4562 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6493 0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6449 -1.5150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5311 -0.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2331 0.1374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5198 -0.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3269 1.6639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0142 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8874 -2.0837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6404 -0.0153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3798 1.6639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9175 0.9234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8158 -0.4812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9241 -0.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1899 -0.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 -0.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8608 1.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2108 0.9234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2113 0.1685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7067 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8070 -1.4283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7120 -2.1079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7804 -0.7619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 -1.3581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 18 2 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 28 1 0 0 0 0 19 22 1 0 0 0 0 20 16 1 6 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 29 1 6 0 0 0 22 31 2 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 24 28 1 0 0 0 0 24 30 1 0 0 0 0 24 33 2 0 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 25 34 2 0 0 0 0 27 30 1 0 0 0 0 28 13 1 6 0 0 0 29 15 1 6 0 0 0 30 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.26
Volume:	498.723
LogP:	6.236
LogD:	4.78
LogS:	-4.35
# Rotatable Bonds:	4
TPSA:	68.28
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	6.092
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.195
MDCK Permeability:	1.7659127479419112e-05
Pgp-inhibitor:	0.214
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	99.40364837646484%
Volume Distribution (VD):	1.986
Pgp-substrate:	2.4068946838378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.94

ADMET: Excretion

Clearance (CL):	9.209
Half-life (T1/2):	0.025

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.004
Carcinogencity:	0.156
Eye Corrosion:	0.55
Eye Irritation:	0.229
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC472699

Natural Product ID:	NPC472699
*Common Name:**	LKIFHVGNUAWISW-MNXVISAMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LKIFHVGNUAWISW-MNXVISAMSA-N
Standard InCHI:	InChI=1S/C30H36O4/c1-18(2)12-13-28-17-20-16-21-26(3,4)14-15-29(21,23(28)32)25(34)30(24(28)33,27(20,5)6)22(31)19-10-8-7-9-11-19/h7-12,20-21H,13-17H2,1-6H3/t20-,21-,28+,29-,30+/m1/s1
SMILES:	CC(=CCC12CC3CC4C(CCC4(C1=O)C(=O)C(C2=O)(C3(C)C)C(=O)C5=CC=CC=C5)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581603
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[493396]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[493396]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[493396]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[493396]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[493396]

☑ 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 NPC472699 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	321
0.1-0.2	1706
0.2-0.3	3413
0.3-0.4	13647
0.4-0.5	18931
0.5-0.6	4033
0.6-0.7	580
0.7-0.8	51
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472700
0.9899	High Similarity	NPC472683
0.9899	High Similarity	NPC472701
0.9899	High Similarity	NPC472696
0.9899	High Similarity	NPC472695
0.9109	High Similarity	NPC474866
0.9109	High Similarity	NPC472691
0.9109	High Similarity	NPC475939
0.9109	High Similarity	NPC471829
0.8909	High Similarity	NPC472697
0.8909	High Similarity	NPC472698
0.8544	High Similarity	NPC109514
0.8515	High Similarity	NPC185208
0.8515	High Similarity	NPC219573
0.8431	Intermediate Similarity	NPC239185
0.84	Intermediate Similarity	NPC59677
0.8365	Intermediate Similarity	NPC472879
0.8365	Intermediate Similarity	NPC476993
0.835	Intermediate Similarity	NPC134882
0.8333	Intermediate Similarity	NPC470252
0.8252	Intermediate Similarity	NPC265220
0.8218	Intermediate Similarity	NPC188844
0.8218	Intermediate Similarity	NPC323420
0.8218	Intermediate Similarity	NPC1682
0.8198	Intermediate Similarity	NPC471481
0.8173	Intermediate Similarity	NPC75724
0.8125	Intermediate Similarity	NPC130591
0.8125	Intermediate Similarity	NPC234637
0.8119	Intermediate Similarity	NPC284475
0.8058	Intermediate Similarity	NPC260233
0.8039	Intermediate Similarity	NPC153885
0.8034	Intermediate Similarity	NPC476234
0.802	Intermediate Similarity	NPC19256
0.8	Intermediate Similarity	NPC49994
0.8	Intermediate Similarity	NPC267262
0.7961	Intermediate Similarity	NPC289883
0.7961	Intermediate Similarity	NPC238219
0.7946	Intermediate Similarity	NPC218855
0.7946	Intermediate Similarity	NPC280789
0.7941	Intermediate Similarity	NPC133461
0.7934	Intermediate Similarity	NPC470648
0.7921	Intermediate Similarity	NPC113307
0.7921	Intermediate Similarity	NPC298115
0.7917	Intermediate Similarity	NPC472693
0.7917	Intermediate Similarity	NPC472694
0.79	Intermediate Similarity	NPC69057
0.7876	Intermediate Similarity	NPC93287
0.7869	Intermediate Similarity	NPC472678
0.7864	Intermediate Similarity	NPC155232
0.7845	Intermediate Similarity	NPC268930
0.7822	Intermediate Similarity	NPC157778
0.7807	Intermediate Similarity	NPC471721
0.7797	Intermediate Similarity	NPC472680
0.7797	Intermediate Similarity	NPC472679
0.7739	Intermediate Similarity	NPC215419
0.7723	Intermediate Similarity	NPC43945
0.7714	Intermediate Similarity	NPC472880
0.7699	Intermediate Similarity	NPC265513
0.7692	Intermediate Similarity	NPC475057
0.7692	Intermediate Similarity	NPC61651
0.7677	Intermediate Similarity	NPC273758
0.7672	Intermediate Similarity	NPC260886
0.767	Intermediate Similarity	NPC173413
0.767	Intermediate Similarity	NPC277277
0.7658	Intermediate Similarity	NPC85560
0.7658	Intermediate Similarity	NPC244933
0.7647	Intermediate Similarity	NPC476225
0.7642	Intermediate Similarity	NPC48992
0.7624	Intermediate Similarity	NPC307
0.7624	Intermediate Similarity	NPC160339
0.7596	Intermediate Similarity	NPC475059
0.7596	Intermediate Similarity	NPC475023
0.7573	Intermediate Similarity	NPC418308
0.757	Intermediate Similarity	NPC240042
0.7551	Intermediate Similarity	NPC477703
0.7551	Intermediate Similarity	NPC190567
0.7551	Intermediate Similarity	NPC164086
0.7541	Intermediate Similarity	NPC472681
0.754	Intermediate Similarity	NPC472692
0.754	Intermediate Similarity	NPC472682
0.75	Intermediate Similarity	NPC294458
0.75	Intermediate Similarity	NPC58872
0.7477	Intermediate Similarity	NPC329282
0.7475	Intermediate Similarity	NPC12936
0.7475	Intermediate Similarity	NPC145053
0.7475	Intermediate Similarity	NPC273033
0.7449	Intermediate Similarity	NPC300205
0.7429	Intermediate Similarity	NPC125226
0.7419	Intermediate Similarity	NPC470649
0.7419	Intermediate Similarity	NPC478107
0.7417	Intermediate Similarity	NPC202015
0.7414	Intermediate Similarity	NPC470253
0.7407	Intermediate Similarity	NPC251579
0.7407	Intermediate Similarity	NPC133135
0.7387	Intermediate Similarity	NPC247976
0.7377	Intermediate Similarity	NPC167323
0.7377	Intermediate Similarity	NPC269923
0.7374	Intermediate Similarity	NPC285716
0.7374	Intermediate Similarity	NPC71664
0.7374	Intermediate Similarity	NPC17408
0.735	Intermediate Similarity	NPC326664
0.7347	Intermediate Similarity	NPC285470
0.7347	Intermediate Similarity	NPC2785
0.7347	Intermediate Similarity	NPC36342
0.7345	Intermediate Similarity	NPC100767
0.7327	Intermediate Similarity	NPC215008
0.7311	Intermediate Similarity	NPC469843
0.7302	Intermediate Similarity	NPC316553
0.7281	Intermediate Similarity	NPC112903
0.7273	Intermediate Similarity	NPC272260
0.7273	Intermediate Similarity	NPC54647
0.7273	Intermediate Similarity	NPC139901
0.7273	Intermediate Similarity	NPC151405
0.7266	Intermediate Similarity	NPC471334
0.7265	Intermediate Similarity	NPC143768
0.7258	Intermediate Similarity	NPC85511
0.7245	Intermediate Similarity	NPC245966
0.7207	Intermediate Similarity	NPC264728
0.72	Intermediate Similarity	NPC478108
0.7193	Intermediate Similarity	NPC83409
0.7193	Intermediate Similarity	NPC185763
0.7193	Intermediate Similarity	NPC37914
0.7184	Intermediate Similarity	NPC252067
0.7182	Intermediate Similarity	NPC120393
0.7172	Intermediate Similarity	NPC103488
0.7143	Intermediate Similarity	NPC294050
0.7143	Intermediate Similarity	NPC328997
0.7143	Intermediate Similarity	NPC153308
0.7132	Intermediate Similarity	NPC470278
0.713	Intermediate Similarity	NPC470007
0.712	Intermediate Similarity	NPC325740
0.7117	Intermediate Similarity	NPC221825
0.7107	Intermediate Similarity	NPC323440
0.7107	Intermediate Similarity	NPC94425
0.7107	Intermediate Similarity	NPC80605
0.7107	Intermediate Similarity	NPC222968
0.7105	Intermediate Similarity	NPC471186
0.7103	Intermediate Similarity	NPC103346
0.7099	Intermediate Similarity	NPC203486
0.7091	Intermediate Similarity	NPC469891
0.7091	Intermediate Similarity	NPC469890
0.7091	Intermediate Similarity	NPC469892
0.7087	Intermediate Similarity	NPC146239
0.7087	Intermediate Similarity	NPC474106
0.7083	Intermediate Similarity	NPC9274
0.708	Intermediate Similarity	NPC329556
0.7075	Intermediate Similarity	NPC325709
0.7071	Intermediate Similarity	NPC9796
0.7071	Intermediate Similarity	NPC179726
0.7063	Intermediate Similarity	NPC79698
0.7054	Intermediate Similarity	NPC133809
0.7054	Intermediate Similarity	NPC136810
0.7054	Intermediate Similarity	NPC25736
0.7054	Intermediate Similarity	NPC128248
0.7034	Intermediate Similarity	NPC292834
0.703	Intermediate Similarity	NPC95868
0.7023	Intermediate Similarity	NPC472656
0.7009	Intermediate Similarity	NPC303967
0.7009	Intermediate Similarity	NPC67585
0.7009	Intermediate Similarity	NPC110420
0.7	Intermediate Similarity	NPC476357
0.7	Intermediate Similarity	NPC469893
0.7	Intermediate Similarity	NPC93181
0.6992	Remote Similarity	NPC476645
0.6992	Remote Similarity	NPC477596
0.699	Remote Similarity	NPC39600
0.699	Remote Similarity	NPC197581
0.6984	Remote Similarity	NPC328107
0.6984	Remote Similarity	NPC51079
0.697	Remote Similarity	NPC126516
0.697	Remote Similarity	NPC329913
0.6961	Remote Similarity	NPC73978
0.6952	Remote Similarity	NPC164526
0.6949	Remote Similarity	NPC137315
0.6939	Remote Similarity	NPC474796
0.6939	Remote Similarity	NPC474797
0.6939	Remote Similarity	NPC329866
0.6937	Remote Similarity	NPC226041
0.693	Remote Similarity	NPC274443
0.6917	Remote Similarity	NPC67377
0.6917	Remote Similarity	NPC477594
0.6911	Remote Similarity	NPC318173
0.6903	Remote Similarity	NPC225079
0.6899	Remote Similarity	NPC115797
0.6899	Remote Similarity	NPC51448
0.6893	Remote Similarity	NPC230068
0.6891	Remote Similarity	NPC186128
0.6885	Remote Similarity	NPC158157
0.6875	Remote Similarity	NPC145052
0.687	Remote Similarity	NPC72915
0.686	Remote Similarity	NPC217111
0.686	Remote Similarity	NPC274839
0.6857	Remote Similarity	NPC123476
0.6842	Remote Similarity	NPC320891
0.6842	Remote Similarity	NPC244427
0.6842	Remote Similarity	NPC48929
0.6842	Remote Similarity	NPC222390
0.6838	Remote Similarity	NPC249811
0.6838	Remote Similarity	NPC203732
0.6837	Remote Similarity	NPC285679

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 NPC472699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	1039
0.2-0.3	1600
0.3-0.4	3748
0.4-0.5	1986
0.5-0.6	439
0.6-0.7	52
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8431	Intermediate Similarity	NPD3495	Discontinued
0.8218	Intermediate Similarity	NPD1508	Approved
0.8218	Intermediate Similarity	NPD7631	Approved
0.8119	Intermediate Similarity	NPD7609	Phase 3
0.8	Intermediate Similarity	NPD7610	Discontinued
0.7981	Intermediate Similarity	NPD1843	Approved
0.7723	Intermediate Similarity	NPD650	Approved
0.7627	Intermediate Similarity	NPD7009	Phase 2
0.7583	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7094	Approved
0.7565	Intermediate Similarity	NPD6858	Approved
0.7475	Intermediate Similarity	NPD942	Approved
0.7339	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7961	Discontinued
0.7117	Intermediate Similarity	NPD2066	Phase 3
0.7094	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1930	Approved
0.708	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1929	Approved
0.7059	Intermediate Similarity	NPD7076	Approved
0.7059	Intermediate Similarity	NPD7077	Approved
0.703	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5951	Approved
0.6972	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3025	Approved
0.6855	Remote Similarity	NPD3024	Approved
0.6842	Remote Similarity	NPD2648	Phase 3
0.6842	Remote Similarity	NPD2196	Discontinued
0.6842	Remote Similarity	NPD2193	Phase 2
0.6842	Remote Similarity	NPD1932	Approved
0.68	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2329	Discontinued
0.6769	Remote Similarity	NPD7084	Phase 3
0.6768	Remote Similarity	NPD4058	Approved
0.6757	Remote Similarity	NPD4094	Approved
0.6757	Remote Similarity	NPD1693	Approved
0.6757	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6049	Phase 2
0.6746	Remote Similarity	NPD3026	Approved
0.6746	Remote Similarity	NPD3023	Approved
0.6729	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5836	Discontinued
0.6637	Remote Similarity	NPD4657	Approved
0.6637	Remote Similarity	NPD4655	Approved
0.6614	Remote Similarity	NPD4879	Approved
0.66	Remote Similarity	NPD4687	Approved
0.66	Remote Similarity	NPD5733	Approved
0.6596	Remote Similarity	NPD7236	Approved
0.6591	Remote Similarity	NPD7055	Discontinued
0.6577	Remote Similarity	NPD1088	Approved
0.6574	Remote Similarity	NPD1087	Approved
0.6552	Remote Similarity	NPD2171	Approved
0.6552	Remote Similarity	NPD6027	Approved
0.6552	Remote Similarity	NPD6024	Approved
0.6542	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1876	Approved
0.6535	Remote Similarity	NPD2932	Approved
0.6525	Remote Similarity	NPD2192	Approved
0.6525	Remote Similarity	NPD1677	Discontinued
0.6525	Remote Similarity	NPD2197	Approved
0.6496	Remote Similarity	NPD3357	Discontinued
0.6493	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4747	Approved
0.6465	Remote Similarity	NPD4691	Approved
0.6446	Remote Similarity	NPD1317	Discontinued
0.6441	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5909	Discontinued
0.6404	Remote Similarity	NPD1989	Approved
0.64	Remote Similarity	NPD5276	Approved
0.6396	Remote Similarity	NPD1086	Approved
0.6396	Remote Similarity	NPD1089	Approved
0.6396	Remote Similarity	NPD1090	Approved
0.6393	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3972	Approved
0.6385	Remote Similarity	NPD4878	Approved
0.6372	Remote Similarity	NPD1202	Approved
0.6372	Remote Similarity	NPD1563	Approved
0.637	Remote Similarity	NPD7239	Suspended
0.6364	Remote Similarity	NPD4137	Phase 3
0.6357	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6647	Phase 2
0.6355	Remote Similarity	NPD3971	Phase 1
0.6348	Remote Similarity	NPD1100	Approved
0.6348	Remote Similarity	NPD1099	Approved
0.632	Remote Similarity	NPD4766	Approved
0.6308	Remote Similarity	NPD6287	Discontinued
0.6306	Remote Similarity	NPD5346	Phase 2
0.6306	Remote Similarity	NPD800	Approved
0.6306	Remote Similarity	NPD5347	Phase 2
0.6303	Remote Similarity	NPD1237	Approved
0.6296	Remote Similarity	NPD7008	Discontinued
0.6279	Remote Similarity	NPD2345	Approved
0.625	Remote Similarity	NPD3672	Approved
0.625	Remote Similarity	NPD3673	Approved
0.6239	Remote Similarity	NPD7798	Approved
0.623	Remote Similarity	NPD2182	Approved
0.6207	Remote Similarity	NPD1564	Approved
0.6207	Remote Similarity	NPD1565	Approved
0.6207	Remote Similarity	NPD1566	Phase 3
0.6204	Remote Similarity	NPD7713	Phase 3
0.6204	Remote Similarity	NPD8032	Phase 2
0.62	Remote Similarity	NPD1673	Approved
0.6195	Remote Similarity	NPD1239	Approved
0.6194	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD164	Approved
0.6147	Remote Similarity	NPD4544	Approved
0.6142	Remote Similarity	NPD3317	Approved
0.6134	Remote Similarity	NPD4803	Discontinued
0.6126	Remote Similarity	NPD4793	Discontinued
0.6119	Remote Similarity	NPD1470	Approved
0.6087	Remote Similarity	NPD6663	Approved
0.6083	Remote Similarity	NPD5765	Approved
0.6077	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6685	Approved
0.6063	Remote Similarity	NPD3867	Phase 2
0.6061	Remote Similarity	NPD1201	Approved
0.6058	Remote Similarity	NPD2754	Discontinued
0.6055	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD664	Approved
0.6042	Remote Similarity	NPD7082	Approved
0.6038	Remote Similarity	NPD225	Approved
0.6038	Remote Similarity	NPD227	Approved
0.6036	Remote Similarity	NPD9257	Approved
0.6036	Remote Similarity	NPD9259	Approved
0.6031	Remote Similarity	NPD4199	Phase 3
0.6029	Remote Similarity	NPD5736	Approved
0.6015	Remote Similarity	NPD3356	Approved
0.6015	Remote Similarity	NPD3355	Approved
0.6014	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD6273	Approved
0.6	Remote Similarity	NPD7741	Discontinued
0.6	Remote Similarity	NPD813	Approved
0.6	Remote Similarity	NPD7259	Approved
0.6	Remote Similarity	NPD7487	Discontinued
0.5986	Remote Similarity	NPD7478	Approved
0.5981	Remote Similarity	NPD9490	Approved
0.5974	Remote Similarity	NPD7057	Phase 3
0.5974	Remote Similarity	NPD7058	Phase 2
0.5971	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD1238	Approved
0.5966	Remote Similarity	NPD742	Approved
0.5959	Remote Similarity	NPD7295	Approved
0.5956	Remote Similarity	NPD2798	Approved
0.5954	Remote Similarity	NPD1245	Approved
0.5952	Remote Similarity	NPD2124	Approved
0.595	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD2629	Approved
0.5938	Remote Similarity	NPD1246	Approved
0.5923	Remote Similarity	NPD5990	Approved
0.5923	Remote Similarity	NPD5991	Approved
0.5923	Remote Similarity	NPD6065	Approved
0.592	Remote Similarity	NPD4234	Approved
0.592	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.592	Remote Similarity	NPD4233	Approved
0.5913	Remote Similarity	NPD1007	Discontinued
0.5909	Remote Similarity	NPD9491	Approved
0.5909	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD1471	Phase 3
0.5899	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5210	Approved
0.5897	Remote Similarity	NPD4629	Approved
0.5896	Remote Similarity	NPD6637	Approved
0.589	Remote Similarity	NPD7003	Approved
0.589	Remote Similarity	NPD8166	Discontinued
0.5882	Remote Similarity	NPD3245	Phase 3
0.5882	Remote Similarity	NPD466	Approved
0.5882	Remote Similarity	NPD5653	Discontinued
0.5882	Remote Similarity	NPD3244	Pre-registration
0.5878	Remote Similarity	NPD6345	Approved
0.5878	Remote Similarity	NPD8165	Discontinued
0.5878	Remote Similarity	NPD6343	Approved
0.5874	Remote Similarity	NPD7305	Phase 1
0.5874	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD226	Approved
0.5867	Remote Similarity	NPD7606	Phase 3
0.5859	Remote Similarity	NPD6010	Discontinued
0.5852	Remote Similarity	NPD3549	Approved
0.5852	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD5159	Phase 2
0.5852	Remote Similarity	NPD3547	Approved
0.5852	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD5157	Phase 1
0.585	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD4980	Approved
0.5827	Remote Similarity	NPD1190	Approved
0.5827	Remote Similarity	NPD6039	Approved
0.5826	Remote Similarity	NPD9258	Approved
0.5826	Remote Similarity	NPD9256	Approved
0.5821	Remote Similarity	NPD5618	Discontinued
0.5818	Remote Similarity	NPD4221	Approved
0.5818	Remote Similarity	NPD4223	Phase 3
0.5814	Remote Similarity	NPD2508	Discontinued

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