NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	3.225
LogD:	3.103
LogS:	-3.426
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	4.544
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	1.8362557966611348e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	95.21407318115234%
Volume Distribution (VD):	0.91
Pgp-substrate:	7.538513660430908%

ADMET: Metabolism

CYP1A2-inhibitor:	0.519
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.527
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.451
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.467

ADMET: Excretion

Clearance (CL):	14.601
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.747
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.904
Carcinogencity:	0.811
Eye Corrosion:	0.006
Eye Irritation:	0.023
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC30486

Natural Product ID:	NPC30486
*Common Name:**	(+)-(5R,7S,9R,10S)-2-Oxocadinan-3,6(11)-Dien-12,7-Olide
IUPAC Name:	(3aS,5R,5aS,9aR)-1,5,8-trimethyl-3a,4,5,5a,6,9a-hexahydrobenzo[e][1]benzofuran-2,7-dione
Synonyms:
Standard InCHIKey:	JCTYUEGJVULBEI-ROBVANNZSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-7-5-13-14(9(3)15(17)18-13)11-4-8(2)12(16)6-10(7)11/h4,7,10-11,13H,5-6H2,1-3H3/t7-,10+,11+,13+/m1/s1
SMILES:	C[C@@H]1C[C@H]2C(=C(C)C(=O)O2)[C@H]2C=C(C)C(=O)C[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506745
PubChem CID:	25016668
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679321]
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[15679321]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[18620454]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26814	Consolida pubescens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9281	Melampodium diffusum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13720	Deparia lancea	Species	Athyriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8654	Digitalis viridiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26814	Consolida pubescens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26870	Nephthea pacifica	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26592	Isaria cretacea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26490	Helenium aromaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13073	Thymus bashkiriensis	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[526449]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	5000.0	nM	PMID[526449]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[526449]

☑ 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 NPC30486 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	187
0.1-0.2	1157
0.2-0.3	4574
0.3-0.4	10849
0.4-0.5	12865
0.5-0.6	7214
0.6-0.7	4656
0.7-0.8	1096
0.8-0.85	80
0.85-0.9	15
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC189311
0.8941	High Similarity	NPC73995
0.8902	High Similarity	NPC193198
0.8837	High Similarity	NPC152467
0.8824	High Similarity	NPC226863
0.8824	High Similarity	NPC215831
0.8721	High Similarity	NPC5509
0.869	High Similarity	NPC177932
0.8675	High Similarity	NPC22611
0.8659	High Similarity	NPC282293
0.8625	High Similarity	NPC316500
0.8621	High Similarity	NPC8062
0.8554	High Similarity	NPC200513
0.8554	High Similarity	NPC178676
0.8539	High Similarity	NPC470697
0.85	High Similarity	NPC473223
0.8471	Intermediate Similarity	NPC110405
0.8462	Intermediate Similarity	NPC84335
0.8462	Intermediate Similarity	NPC38530
0.8444	Intermediate Similarity	NPC183012
0.8434	Intermediate Similarity	NPC475665
0.8427	Intermediate Similarity	NPC475657
0.8427	Intermediate Similarity	NPC139692
0.8427	Intermediate Similarity	NPC115021
0.8415	Intermediate Similarity	NPC150646
0.8395	Intermediate Similarity	NPC41780
0.8395	Intermediate Similarity	NPC187568
0.8395	Intermediate Similarity	NPC189206
0.8372	Intermediate Similarity	NPC220478
0.8353	Intermediate Similarity	NPC475100
0.8353	Intermediate Similarity	NPC149869
0.8333	Intermediate Similarity	NPC471218
0.8333	Intermediate Similarity	NPC186276
0.8333	Intermediate Similarity	NPC477130
0.8333	Intermediate Similarity	NPC477129
0.8333	Intermediate Similarity	NPC38830
0.8333	Intermediate Similarity	NPC84893
0.8315	Intermediate Similarity	NPC473944
0.8315	Intermediate Similarity	NPC186363
0.8315	Intermediate Similarity	NPC233345
0.8313	Intermediate Similarity	NPC195424
0.8313	Intermediate Similarity	NPC268827
0.8293	Intermediate Similarity	NPC471220
0.8293	Intermediate Similarity	NPC128276
0.828	Intermediate Similarity	NPC476299
0.828	Intermediate Similarity	NPC474012
0.8276	Intermediate Similarity	NPC312561
0.8256	Intermediate Similarity	NPC86316
0.8256	Intermediate Similarity	NPC65661
0.8256	Intermediate Similarity	NPC106416
0.8256	Intermediate Similarity	NPC476678
0.8242	Intermediate Similarity	NPC127197
0.8235	Intermediate Similarity	NPC118423
0.8202	Intermediate Similarity	NPC220454
0.8202	Intermediate Similarity	NPC212679
0.8202	Intermediate Similarity	NPC51486
0.8202	Intermediate Similarity	NPC469595
0.8182	Intermediate Similarity	NPC472302
0.8182	Intermediate Similarity	NPC477128
0.8171	Intermediate Similarity	NPC57744
0.8152	Intermediate Similarity	NPC234993
0.8152	Intermediate Similarity	NPC134072
0.8152	Intermediate Similarity	NPC242848
0.814	Intermediate Similarity	NPC159635
0.8132	Intermediate Similarity	NPC476596
0.8125	Intermediate Similarity	NPC189616
0.8118	Intermediate Similarity	NPC268122
0.8118	Intermediate Similarity	NPC226988
0.8111	Intermediate Similarity	NPC49420
0.8111	Intermediate Similarity	NPC472814
0.8111	Intermediate Similarity	NPC177037
0.8095	Intermediate Similarity	NPC271104
0.809	Intermediate Similarity	NPC174342
0.809	Intermediate Similarity	NPC168131
0.809	Intermediate Similarity	NPC284561
0.8085	Intermediate Similarity	NPC472644
0.8085	Intermediate Similarity	NPC471413
0.8085	Intermediate Similarity	NPC201406
0.8085	Intermediate Similarity	NPC117685
0.8072	Intermediate Similarity	NPC35574
0.8072	Intermediate Similarity	NPC184737
0.8065	Intermediate Similarity	NPC474343
0.8065	Intermediate Similarity	NPC110937
0.8065	Intermediate Similarity	NPC253826
0.8065	Intermediate Similarity	NPC2049
0.8049	Intermediate Similarity	NPC40353
0.8049	Intermediate Similarity	NPC27205
0.8046	Intermediate Similarity	NPC323765
0.8046	Intermediate Similarity	NPC474013
0.8043	Intermediate Similarity	NPC295347
0.8043	Intermediate Similarity	NPC470974
0.8043	Intermediate Similarity	NPC470978
0.8023	Intermediate Similarity	NPC222358
0.8023	Intermediate Similarity	NPC194637
0.8023	Intermediate Similarity	NPC297398
0.8022	Intermediate Similarity	NPC476597
0.8022	Intermediate Similarity	NPC476598
0.8022	Intermediate Similarity	NPC472303
0.8	Intermediate Similarity	NPC474842
0.8	Intermediate Similarity	NPC194028
0.8	Intermediate Similarity	NPC472643
0.8	Intermediate Similarity	NPC471818
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC161638
0.8	Intermediate Similarity	NPC42470
0.8	Intermediate Similarity	NPC232426
0.8	Intermediate Similarity	NPC38642
0.8	Intermediate Similarity	NPC471325
0.8	Intermediate Similarity	NPC168319
0.8	Intermediate Similarity	NPC475965
0.8	Intermediate Similarity	NPC281942
0.8	Intermediate Similarity	NPC158488
0.7979	Intermediate Similarity	NPC252295
0.7979	Intermediate Similarity	NPC108368
0.7979	Intermediate Similarity	NPC57079
0.7978	Intermediate Similarity	NPC277771
0.7976	Intermediate Similarity	NPC178277
0.7957	Intermediate Similarity	NPC202833
0.7957	Intermediate Similarity	NPC29952
0.7955	Intermediate Similarity	NPC168248
0.7955	Intermediate Similarity	NPC195640
0.7952	Intermediate Similarity	NPC65603
0.7952	Intermediate Similarity	NPC472300
0.7935	Intermediate Similarity	NPC250075
0.7931	Intermediate Similarity	NPC96055
0.7931	Intermediate Similarity	NPC71626
0.7931	Intermediate Similarity	NPC474359
0.7931	Intermediate Similarity	NPC219011
0.7927	Intermediate Similarity	NPC65650
0.7917	Intermediate Similarity	NPC162973
0.7912	Intermediate Similarity	NPC289479
0.7912	Intermediate Similarity	NPC303697
0.7912	Intermediate Similarity	NPC65513
0.7912	Intermediate Similarity	NPC141831
0.7912	Intermediate Similarity	NPC252433
0.7907	Intermediate Similarity	NPC94200
0.7895	Intermediate Similarity	NPC473219
0.7895	Intermediate Similarity	NPC54705
0.7895	Intermediate Similarity	NPC476274
0.7895	Intermediate Similarity	NPC470761
0.7889	Intermediate Similarity	NPC177141
0.7889	Intermediate Similarity	NPC50488
0.7889	Intermediate Similarity	NPC288699
0.7889	Intermediate Similarity	NPC251528
0.7889	Intermediate Similarity	NPC474396
0.7889	Intermediate Similarity	NPC173042
0.7872	Intermediate Similarity	NPC208094
0.7872	Intermediate Similarity	NPC476768
0.7865	Intermediate Similarity	NPC477228
0.7865	Intermediate Similarity	NPC181327
0.7857	Intermediate Similarity	NPC299235
0.7849	Intermediate Similarity	NPC209355
0.7849	Intermediate Similarity	NPC33473
0.7849	Intermediate Similarity	NPC316215
0.7841	Intermediate Similarity	NPC52628
0.7835	Intermediate Similarity	NPC254202
0.7835	Intermediate Similarity	NPC180204
0.7835	Intermediate Similarity	NPC471365
0.7835	Intermediate Similarity	NPC132395
0.7835	Intermediate Similarity	NPC112009
0.7835	Intermediate Similarity	NPC471364
0.7831	Intermediate Similarity	NPC235906
0.7831	Intermediate Similarity	NPC472305
0.7826	Intermediate Similarity	NPC229976
0.7826	Intermediate Similarity	NPC166346
0.7826	Intermediate Similarity	NPC79117
0.7816	Intermediate Similarity	NPC470047
0.7816	Intermediate Similarity	NPC474193
0.7816	Intermediate Similarity	NPC470046
0.7816	Intermediate Similarity	NPC12283
0.7812	Intermediate Similarity	NPC476223
0.7812	Intermediate Similarity	NPC224720
0.7812	Intermediate Similarity	NPC310981
0.7812	Intermediate Similarity	NPC476240
0.7805	Intermediate Similarity	NPC117746
0.7805	Intermediate Similarity	NPC20025
0.7805	Intermediate Similarity	NPC294434
0.7805	Intermediate Similarity	NPC259599
0.7805	Intermediate Similarity	NPC15499
0.7802	Intermediate Similarity	NPC221111
0.7802	Intermediate Similarity	NPC280149
0.7802	Intermediate Similarity	NPC182136
0.7802	Intermediate Similarity	NPC469372
0.7802	Intermediate Similarity	NPC310479
0.7802	Intermediate Similarity	NPC328141
0.7802	Intermediate Similarity	NPC273199
0.7802	Intermediate Similarity	NPC159748
0.7802	Intermediate Similarity	NPC101651
0.7791	Intermediate Similarity	NPC325031
0.7789	Intermediate Similarity	NPC216478
0.7789	Intermediate Similarity	NPC316598
0.7789	Intermediate Similarity	NPC23364
0.7789	Intermediate Similarity	NPC478056
0.7789	Intermediate Similarity	NPC176845
0.7778	Intermediate Similarity	NPC93411
0.7778	Intermediate Similarity	NPC136879
0.7778	Intermediate Similarity	NPC24816
0.7778	Intermediate Similarity	NPC477302
0.7766	Intermediate Similarity	NPC154526
0.7766	Intermediate Similarity	NPC472363

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 NPC30486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1482
0.2-0.3	3761
0.3-0.4	2453
0.4-0.5	829
0.5-0.6	277
0.6-0.7	159
0.7-0.8	15
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD1694	Approved
0.8554	High Similarity	NPD4752	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7521	Approved
0.7955	Intermediate Similarity	NPD6684	Approved
0.7955	Intermediate Similarity	NPD7146	Approved
0.7955	Intermediate Similarity	NPD6409	Approved
0.7955	Intermediate Similarity	NPD5330	Approved
0.7955	Intermediate Similarity	NPD7334	Approved
0.7778	Intermediate Similarity	NPD6903	Approved
0.7778	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3573	Approved
0.7582	Intermediate Similarity	NPD6672	Approved
0.7582	Intermediate Similarity	NPD5737	Approved
0.7553	Intermediate Similarity	NPD7900	Approved
0.7553	Intermediate Similarity	NPD7748	Approved
0.7553	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5693	Phase 1
0.7423	Intermediate Similarity	NPD7638	Approved
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.7347	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD7640	Approved
0.734	Intermediate Similarity	NPD7515	Phase 2
0.732	Intermediate Similarity	NPD7902	Approved
0.7263	Intermediate Similarity	NPD6399	Phase 3
0.7245	Intermediate Similarity	NPD4225	Approved
0.7204	Intermediate Similarity	NPD5208	Approved
0.7158	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7128	Intermediate Similarity	NPD5328	Approved
0.7128	Intermediate Similarity	NPD6904	Approved
0.7128	Intermediate Similarity	NPD6673	Approved
0.7128	Intermediate Similarity	NPD6080	Approved
0.7113	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5695	Phase 3
0.7111	Intermediate Similarity	NPD3667	Approved
0.7093	Intermediate Similarity	NPD8039	Approved
0.7087	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5697	Approved
0.7053	Intermediate Similarity	NPD5207	Approved
0.7053	Intermediate Similarity	NPD5692	Phase 3
0.7019	Intermediate Similarity	NPD6686	Approved
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.701	Intermediate Similarity	NPD6001	Approved
0.699	Remote Similarity	NPD6675	Approved
0.699	Remote Similarity	NPD6008	Approved
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD5739	Approved
0.6989	Remote Similarity	NPD6098	Approved
0.6979	Remote Similarity	NPD5694	Approved
0.6979	Remote Similarity	NPD6050	Approved
0.697	Remote Similarity	NPD6083	Phase 2
0.697	Remote Similarity	NPD6084	Phase 2
0.6957	Remote Similarity	NPD4786	Approved
0.6957	Remote Similarity	NPD3668	Phase 3
0.6952	Remote Similarity	NPD6014	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6051	Approved
0.6923	Remote Similarity	NPD5209	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6907	Remote Similarity	NPD4202	Approved
0.69	Remote Similarity	NPD5696	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5221	Approved
0.6869	Remote Similarity	NPD5222	Approved
0.6869	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7320	Approved
0.6829	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4691	Approved
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6847	Approved
0.6809	Remote Similarity	NPD4519	Discontinued
0.6809	Remote Similarity	NPD5279	Phase 3
0.6809	Remote Similarity	NPD4623	Approved
0.68	Remote Similarity	NPD5173	Approved
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD6372	Approved
0.6771	Remote Similarity	NPD1695	Approved
0.6768	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6739	Remote Similarity	NPD4223	Phase 3
0.6739	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6706	Remote Similarity	NPD4137	Phase 3
0.6703	Remote Similarity	NPD4695	Discontinued
0.6702	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5785	Approved
0.67	Remote Similarity	NPD4697	Phase 3
0.6699	Remote Similarity	NPD5211	Phase 2
0.6699	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6634	Remote Similarity	NPD4755	Approved
0.6633	Remote Similarity	NPD5281	Approved
0.6633	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5690	Phase 2
0.6628	Remote Similarity	NPD4747	Approved
0.6606	Remote Similarity	NPD6053	Discontinued
0.6602	Remote Similarity	NPD5223	Approved
0.66	Remote Similarity	NPD5654	Approved
0.6598	Remote Similarity	NPD6101	Approved
0.6598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4753	Phase 2
0.6596	Remote Similarity	NPD4197	Approved
0.6591	Remote Similarity	NPD4058	Approved
0.6577	Remote Similarity	NPD6274	Approved
0.6577	Remote Similarity	NPD6868	Approved
0.6571	Remote Similarity	NPD5141	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD5224	Approved
0.6538	Remote Similarity	NPD5226	Approved
0.6538	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD4633	Approved
0.6535	Remote Similarity	NPD7732	Phase 3
0.6531	Remote Similarity	NPD6698	Approved
0.6531	Remote Similarity	NPD46	Approved
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5363	Approved
0.6526	Remote Similarity	NPD5329	Approved
0.6526	Remote Similarity	NPD1696	Phase 3
0.6518	Remote Similarity	NPD6317	Approved
0.6505	Remote Similarity	NPD4700	Approved
0.6484	Remote Similarity	NPD3617	Approved
0.6476	Remote Similarity	NPD5175	Approved
0.6476	Remote Similarity	NPD5174	Approved
0.6471	Remote Similarity	NPD5959	Approved
0.6465	Remote Similarity	NPD8034	Phase 2
0.6465	Remote Similarity	NPD6411	Approved
0.6465	Remote Similarity	NPD8035	Phase 2
0.646	Remote Similarity	NPD6335	Approved
0.646	Remote Similarity	NPD6313	Approved
0.646	Remote Similarity	NPD6314	Approved
0.6458	Remote Similarity	NPD5280	Approved
0.6458	Remote Similarity	NPD4688	Approved
0.6458	Remote Similarity	NPD4694	Approved
0.6458	Remote Similarity	NPD4689	Approved
0.6458	Remote Similarity	NPD5205	Approved
0.6458	Remote Similarity	NPD4693	Phase 3
0.6458	Remote Similarity	NPD4690	Approved
0.6458	Remote Similarity	NPD4138	Approved
0.6436	Remote Similarity	NPD4629	Approved
0.6436	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7101	Approved
0.6404	Remote Similarity	NPD7100	Approved
0.6404	Remote Similarity	NPD5733	Approved
0.6404	Remote Similarity	NPD4687	Approved
0.6373	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6009	Approved
0.6364	Remote Similarity	NPD5276	Approved
0.6356	Remote Similarity	NPD7507	Approved
0.6348	Remote Similarity	NPD6319	Approved
0.6346	Remote Similarity	NPD6648	Approved
0.6346	Remote Similarity	NPD6404	Discontinued
0.6321	Remote Similarity	NPD6052	Approved
0.6321	Remote Similarity	NPD4754	Approved
0.6316	Remote Similarity	NPD5362	Discontinued
0.6316	Remote Similarity	NPD7154	Phase 3
0.6304	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD6614	Approved
0.6293	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5983	Phase 2
0.6286	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD7094	Approved
0.625	Remote Similarity	NPD6858	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD5168	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6237	Remote Similarity	NPD4195	Approved
0.6214	Remote Similarity	NPD7614	Phase 1
0.6211	Remote Similarity	NPD6435	Approved
0.6211	Remote Similarity	NPD4269	Approved
0.6211	Remote Similarity	NPD4270	Approved
0.6207	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4767	Approved
0.6204	Remote Similarity	NPD4768	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.6196	Remote Similarity	NPD4756	Discovery

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