NPASS Compound

Structure

CID251528 OpenBabel06191716052D 23 25 0 0 1 0 0 0 0 0999 V2000 3.3147 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7788 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9128 -0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 -1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 6 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	5.17
LogD:	4.206
LogS:	-4.209
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	4.292
Fsp3:	0.7
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:	-4.856
MDCK Permeability:	2.010277603403665e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.665
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	95.54634094238281%
Volume Distribution (VD):	1.391
Pgp-substrate:	3.4214425086975098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.277
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.427
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	10.762
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.67
Maximum Recommended Daily Dose:	0.735
Skin Sensitization:	0.686
Carcinogencity:	0.9
Eye Corrosion:	0.055
Eye Irritation:	0.481
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC251528

Natural Product ID:	NPC251528
*Common Name:**	Coronarin C
IUPAC Name:	4-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
Synonyms:	Coronarin C
Standard InCHIKey:	RNPDONJEBKWTIQ-SEVYOHKTSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-6-9-16-19(2,3)10-5-11-20(16,4)15(13)8-7-14-12-17(21)23-18(14)22/h12,15-17,21H,1,5-11H2,2-4H3/t15-,16-,17?,20+/m0/s1
SMILES:	OC1OC(=O)C(=C1)CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288154
PubChem CID:	52947374
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO41076	Amomum villosum	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31710213]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	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
GI50	4
IC50	2
Others	5

Activity Type	# Activity
Cell Line	9
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	4800.0	nM	PMID[572701]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	9500.0	nM	PMID[572701]
NPT136	Cell Line	SK-N-SH	Homo sapiens	GI50	=	25800.0	nM	PMID[572701]
NPT136	Cell Line	SK-N-SH	Homo sapiens	LC50	=	33700.0	nM	PMID[572701]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	32600.0	nM	PMID[572701]
NPT83	Cell Line	MCF7	Homo sapiens	LC50	=	40700.0	nM	PMID[572701]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	36300.0	nM	PMID[572701]
NPT165	Cell Line	HeLa	Homo sapiens	LC50	=	45900.0	nM	PMID[572701]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	25800.0	nM	PMID[572702]
NPT2	Others	Unspecified		Inhibition	=	87.4	%	PMID[572702]
NPT2	Others	Unspecified		IC50	=	17500.0	nM	PMID[572702]

☑ 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 NPC251528 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	182
0.1-0.2	1139
0.2-0.3	4533
0.3-0.4	11398
0.4-0.5	11534
0.5-0.6	6962
0.6-0.7	5742
0.7-0.8	1067
0.8-0.85	114
0.85-0.9	18
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC477783
0.9647	High Similarity	NPC477782
0.9286	High Similarity	NPC86316
0.9286	High Similarity	NPC106416
0.9222	High Similarity	NPC475709
0.9059	High Similarity	NPC65661
0.8953	High Similarity	NPC474062
0.8929	High Similarity	NPC200513
0.8876	High Similarity	NPC472814
0.8876	High Similarity	NPC177037
0.8864	High Similarity	NPC174342
0.8851	High Similarity	NPC475678
0.8837	High Similarity	NPC42586
0.8837	High Similarity	NPC473251
0.8817	High Similarity	NPC477720
0.8778	High Similarity	NPC166346
0.8764	High Similarity	NPC51486
0.875	High Similarity	NPC472810
0.875	High Similarity	NPC472809
0.8696	High Similarity	NPC470801
0.8652	High Similarity	NPC5509
0.8571	High Similarity	NPC472303
0.8571	High Similarity	NPC139692
0.8571	High Similarity	NPC115021
0.8556	High Similarity	NPC281942
0.8556	High Similarity	NPC232426
0.8526	High Similarity	NPC63249
0.8506	High Similarity	NPC71626
0.8495	Intermediate Similarity	NPC134072
0.8495	Intermediate Similarity	NPC242848
0.8495	Intermediate Similarity	NPC234993
0.8495	Intermediate Similarity	NPC325960
0.8495	Intermediate Similarity	NPC319692
0.8478	Intermediate Similarity	NPC475572
0.8478	Intermediate Similarity	NPC474554
0.8462	Intermediate Similarity	NPC472811
0.8462	Intermediate Similarity	NPC179517
0.8462	Intermediate Similarity	NPC65513
0.8462	Intermediate Similarity	NPC289479
0.8462	Intermediate Similarity	NPC165904
0.8462	Intermediate Similarity	NPC141831
0.8444	Intermediate Similarity	NPC470734
0.8438	Intermediate Similarity	NPC134077
0.8427	Intermediate Similarity	NPC312561
0.8421	Intermediate Similarity	NPC476767
0.8409	Intermediate Similarity	NPC189311
0.8409	Intermediate Similarity	NPC217394
0.8391	Intermediate Similarity	NPC311070
0.8387	Intermediate Similarity	NPC209355
0.8372	Intermediate Similarity	NPC229584
0.8372	Intermediate Similarity	NPC40228
0.8372	Intermediate Similarity	NPC14203
0.837	Intermediate Similarity	NPC472812
0.837	Intermediate Similarity	NPC469939
0.8298	Intermediate Similarity	NPC240673
0.8298	Intermediate Similarity	NPC17578
0.828	Intermediate Similarity	NPC474555
0.828	Intermediate Similarity	NPC470255
0.828	Intermediate Similarity	NPC324078
0.828	Intermediate Similarity	NPC469697
0.8261	Intermediate Similarity	NPC477122
0.8242	Intermediate Similarity	NPC50488
0.8242	Intermediate Similarity	NPC168131
0.8242	Intermediate Similarity	NPC474396
0.8235	Intermediate Similarity	NPC198240
0.8235	Intermediate Similarity	NPC239098
0.8211	Intermediate Similarity	NPC474343
0.8211	Intermediate Similarity	NPC257726
0.8211	Intermediate Similarity	NPC204054
0.8202	Intermediate Similarity	NPC474860
0.8202	Intermediate Similarity	NPC471300
0.8202	Intermediate Similarity	NPC30984
0.82	Intermediate Similarity	NPC177524
0.82	Intermediate Similarity	NPC219900
0.82	Intermediate Similarity	NPC476765
0.82	Intermediate Similarity	NPC392
0.8191	Intermediate Similarity	NPC472441
0.8191	Intermediate Similarity	NPC293052
0.8182	Intermediate Similarity	NPC472440
0.8182	Intermediate Similarity	NPC22611
0.8172	Intermediate Similarity	NPC242069
0.8152	Intermediate Similarity	NPC253186
0.8152	Intermediate Similarity	NPC182136
0.8144	Intermediate Similarity	NPC471075
0.8132	Intermediate Similarity	NPC474629
0.8132	Intermediate Similarity	NPC226863
0.8125	Intermediate Similarity	NPC474440
0.8125	Intermediate Similarity	NPC473154
0.8118	Intermediate Similarity	NPC316500
0.8118	Intermediate Similarity	NPC61952
0.8105	Intermediate Similarity	NPC29952
0.8105	Intermediate Similarity	NPC162346
0.809	Intermediate Similarity	NPC149869
0.809	Intermediate Similarity	NPC471302
0.809	Intermediate Similarity	NPC475100
0.8085	Intermediate Similarity	NPC104925
0.8085	Intermediate Similarity	NPC298973
0.8068	Intermediate Similarity	NPC471296
0.8065	Intermediate Similarity	NPC470113
0.8046	Intermediate Similarity	NPC10636
0.8041	Intermediate Similarity	NPC472644
0.8041	Intermediate Similarity	NPC201406
0.8039	Intermediate Similarity	NPC476766
0.8023	Intermediate Similarity	NPC59436
0.8021	Intermediate Similarity	NPC476253
0.8021	Intermediate Similarity	NPC253826
0.8021	Intermediate Similarity	NPC477719
0.8021	Intermediate Similarity	NPC477718
0.8021	Intermediate Similarity	NPC208094
0.8	Intermediate Similarity	NPC472442
0.8	Intermediate Similarity	NPC329630
0.7979	Intermediate Similarity	NPC472871
0.7978	Intermediate Similarity	NPC193198
0.7978	Intermediate Similarity	NPC215893
0.7978	Intermediate Similarity	NPC469
0.7959	Intermediate Similarity	NPC472643
0.7959	Intermediate Similarity	NPC471412
0.7959	Intermediate Similarity	NPC303559
0.7957	Intermediate Similarity	NPC310479
0.7957	Intermediate Similarity	NPC8062
0.7941	Intermediate Similarity	NPC476759
0.7938	Intermediate Similarity	NPC316598
0.7935	Intermediate Similarity	NPC472302
0.7935	Intermediate Similarity	NPC104560
0.7935	Intermediate Similarity	NPC472870
0.7917	Intermediate Similarity	NPC112654
0.7912	Intermediate Similarity	NPC329692
0.7912	Intermediate Similarity	NPC131813
0.7907	Intermediate Similarity	NPC473756
0.7895	Intermediate Similarity	NPC476415
0.7895	Intermediate Similarity	NPC57117
0.7889	Intermediate Similarity	NPC30486
0.7889	Intermediate Similarity	NPC472864
0.7889	Intermediate Similarity	NPC248758
0.7889	Intermediate Similarity	NPC470800
0.7889	Intermediate Similarity	NPC19849
0.7889	Intermediate Similarity	NPC471301
0.7879	Intermediate Similarity	NPC476769
0.7872	Intermediate Similarity	NPC329842
0.7872	Intermediate Similarity	NPC476187
0.7872	Intermediate Similarity	NPC72845
0.7872	Intermediate Similarity	NPC303697
0.7865	Intermediate Similarity	NPC186276
0.7865	Intermediate Similarity	NPC471298
0.7865	Intermediate Similarity	NPC94200
0.7857	Intermediate Similarity	NPC477716
0.7857	Intermediate Similarity	NPC477721
0.7857	Intermediate Similarity	NPC471413
0.7857	Intermediate Similarity	NPC324841
0.7857	Intermediate Similarity	NPC476299
0.7857	Intermediate Similarity	NPC117685
0.7857	Intermediate Similarity	NPC474012
0.7849	Intermediate Similarity	NPC66344
0.7841	Intermediate Similarity	NPC195424
0.7835	Intermediate Similarity	NPC476768
0.7835	Intermediate Similarity	NPC76266
0.7822	Intermediate Similarity	NPC127790
0.7816	Intermediate Similarity	NPC471220
0.7812	Intermediate Similarity	NPC183012
0.7812	Intermediate Similarity	NPC295347
0.7812	Intermediate Similarity	NPC476487
0.7812	Intermediate Similarity	NPC476488
0.7802	Intermediate Similarity	NPC283733
0.7802	Intermediate Similarity	NPC52628
0.78	Intermediate Similarity	NPC112009
0.7789	Intermediate Similarity	NPC151722
0.7789	Intermediate Similarity	NPC152778
0.7789	Intermediate Similarity	NPC476416
0.7789	Intermediate Similarity	NPC470656
0.7789	Intermediate Similarity	NPC475657
0.7789	Intermediate Similarity	NPC162615
0.7789	Intermediate Similarity	NPC205034
0.7778	Intermediate Similarity	NPC477717
0.7778	Intermediate Similarity	NPC471297
0.7778	Intermediate Similarity	NPC97913
0.7778	Intermediate Similarity	NPC42476
0.7766	Intermediate Similarity	NPC476369
0.7766	Intermediate Similarity	NPC472866
0.7766	Intermediate Similarity	NPC476437
0.7766	Intermediate Similarity	NPC78973
0.7766	Intermediate Similarity	NPC101651
0.7766	Intermediate Similarity	NPC221111
0.7766	Intermediate Similarity	NPC280149
0.7766	Intermediate Similarity	NPC159748
0.7765	Intermediate Similarity	NPC20025
0.7755	Intermediate Similarity	NPC57079
0.7755	Intermediate Similarity	NPC108368
0.7755	Intermediate Similarity	NPC98868
0.7755	Intermediate Similarity	NPC23364
0.7753	Intermediate Similarity	NPC282293
0.7753	Intermediate Similarity	NPC90055
0.7753	Intermediate Similarity	NPC325031
0.7742	Intermediate Similarity	NPC196407
0.7742	Intermediate Similarity	NPC472378
0.7732	Intermediate Similarity	NPC202833
0.7732	Intermediate Similarity	NPC473153
0.7727	Intermediate Similarity	NPC150646
0.7727	Intermediate Similarity	NPC242767
0.7723	Intermediate Similarity	NPC476763
0.7723	Intermediate Similarity	NPC476764

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 NPC251528 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1415
0.2-0.3	3776
0.3-0.4	2539
0.4-0.5	781
0.5-0.6	279
0.6-0.7	178
0.7-0.8	24
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD4752	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD6686	Approved
0.7576	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7419	Intermediate Similarity	NPD1694	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7188	Intermediate Similarity	NPD6903	Approved
0.7188	Intermediate Similarity	NPD5737	Approved
0.7188	Intermediate Similarity	NPD6672	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.7128	Intermediate Similarity	NPD3666	Approved
0.7128	Intermediate Similarity	NPD3133	Approved
0.7128	Intermediate Similarity	NPD3665	Phase 1
0.7079	Intermediate Similarity	NPD8039	Approved
0.7041	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD4623	Approved
0.6979	Remote Similarity	NPD3618	Phase 1
0.6979	Remote Similarity	NPD4519	Discontinued
0.697	Remote Similarity	NPD7515	Phase 2
0.6964	Remote Similarity	NPD7115	Discovery
0.6931	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD7507	Approved
0.6916	Remote Similarity	NPD6412	Phase 2
0.6915	Remote Similarity	NPD3667	Approved
0.6907	Remote Similarity	NPD3573	Approved
0.69	Remote Similarity	NPD6399	Phase 3
0.6893	Remote Similarity	NPD5696	Approved
0.6882	Remote Similarity	NPD4695	Discontinued
0.6857	Remote Similarity	NPD7632	Discontinued
0.6837	Remote Similarity	NPD5208	Approved
0.6804	Remote Similarity	NPD5279	Phase 3
0.68	Remote Similarity	NPD6079	Approved
0.6796	Remote Similarity	NPD7902	Approved
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4786	Approved
0.6768	Remote Similarity	NPD6673	Approved
0.6768	Remote Similarity	NPD5328	Approved
0.6768	Remote Similarity	NPD4753	Phase 2
0.6768	Remote Similarity	NPD6080	Approved
0.6768	Remote Similarity	NPD6904	Approved
0.6765	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5697	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.675	Remote Similarity	NPD7319	Approved
0.6737	Remote Similarity	NPD4221	Approved
0.6737	Remote Similarity	NPD4223	Phase 3
0.6697	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6634	Remote Similarity	NPD7637	Suspended
0.6633	Remote Similarity	NPD6098	Approved
0.6609	Remote Similarity	NPD7328	Approved
0.6609	Remote Similarity	NPD7327	Approved
0.6606	Remote Similarity	NPD5701	Approved
0.6602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5210	Approved
0.6602	Remote Similarity	NPD4629	Approved
0.66	Remote Similarity	NPD6051	Approved
0.6598	Remote Similarity	NPD4197	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6883	Approved
0.6569	Remote Similarity	NPD4202	Approved
0.6569	Remote Similarity	NPD5778	Approved
0.6569	Remote Similarity	NPD5779	Approved
0.6562	Remote Similarity	NPD5209	Approved
0.6552	Remote Similarity	NPD7516	Approved
0.6545	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD5211	Phase 2
0.6538	Remote Similarity	NPD5222	Approved
0.6538	Remote Similarity	NPD5221	Approved
0.6538	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD46	Approved
0.6535	Remote Similarity	NPD5692	Phase 3
0.6535	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD5207	Approved
0.6531	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5363	Approved
0.6531	Remote Similarity	NPD5329	Approved
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6505	Remote Similarity	NPD6001	Approved
0.6496	Remote Similarity	NPD8377	Approved
0.6496	Remote Similarity	NPD8294	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6495	Remote Similarity	NPD4788	Approved
0.6495	Remote Similarity	NPD5362	Discontinued
0.6489	Remote Similarity	NPD3617	Approved
0.6486	Remote Similarity	NPD6373	Approved
0.6486	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD5173	Approved
0.6471	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD5284	Approved
0.6471	Remote Similarity	NPD5281	Approved
0.6471	Remote Similarity	NPD6050	Approved
0.6471	Remote Similarity	NPD5694	Approved
0.6465	Remote Similarity	NPD4688	Approved
0.6465	Remote Similarity	NPD4690	Approved
0.6465	Remote Similarity	NPD4689	Approved
0.6465	Remote Similarity	NPD4693	Phase 3
0.6465	Remote Similarity	NPD5690	Phase 2
0.6465	Remote Similarity	NPD5205	Approved
0.6465	Remote Similarity	NPD4138	Approved
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8297	Approved
0.6455	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4691	Approved
0.6441	Remote Similarity	NPD8378	Approved
0.6441	Remote Similarity	NPD8380	Approved
0.6441	Remote Similarity	NPD8335	Approved
0.6441	Remote Similarity	NPD7503	Approved
0.6441	Remote Similarity	NPD8379	Approved
0.6441	Remote Similarity	NPD8296	Approved
0.6441	Remote Similarity	NPD8033	Approved
0.6436	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3668	Phase 3
0.6429	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8133	Approved
0.6381	Remote Similarity	NPD4697	Phase 3
0.6379	Remote Similarity	NPD6009	Approved
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5285	Approved
0.6355	Remote Similarity	NPD5286	Approved
0.6355	Remote Similarity	NPD4696	Approved
0.6333	Remote Similarity	NPD4137	Phase 3
0.6321	Remote Similarity	NPD4755	Approved
0.6316	Remote Similarity	NPD6053	Discontinued
0.6311	Remote Similarity	NPD8034	Phase 2
0.6311	Remote Similarity	NPD8035	Phase 2
0.63	Remote Similarity	NPD5280	Approved
0.63	Remote Similarity	NPD4694	Approved
0.6296	Remote Similarity	NPD5223	Approved
0.6293	Remote Similarity	NPD6274	Approved
0.6293	Remote Similarity	NPD6868	Approved
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4747	Approved
0.6261	Remote Similarity	NPD4632	Approved
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD5224	Approved
0.6239	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD6317	Approved
0.6237	Remote Similarity	NPD4058	Approved
0.6226	Remote Similarity	NPD7732	Phase 3
0.6226	Remote Similarity	NPD7614	Phase 1
0.6224	Remote Similarity	NPD4270	Approved
0.6224	Remote Similarity	NPD4269	Approved
0.6216	Remote Similarity	NPD6008	Approved
0.6204	Remote Similarity	NPD4700	Approved
0.62	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1696	Phase 3
0.6198	Remote Similarity	NPD8328	Phase 3
0.6195	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6314	Approved
0.6186	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD6313	Approved
0.6182	Remote Similarity	NPD5174	Approved
0.6182	Remote Similarity	NPD5175	Approved
0.6179	Remote Similarity	NPD8293	Discontinued
0.6162	Remote Similarity	NPD6695	Phase 3
0.6148	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD5344	Discontinued
0.6142	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5786	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