NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	272.862
LogP:	0.865
LogD:	1.249
LogS:	-2.726
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.818
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.661
MDCK Permeability:	4.451688437256962e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.296
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.578
Plasma Protein Binding (PPB):	79.43940734863281%
Volume Distribution (VD):	1.017
Pgp-substrate:	23.676952362060547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	7.668
Half-life (T1/2):	0.581

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.728
Skin Sensitization:	0.788
Carcinogencity:	0.572
Eye Corrosion:	0.042
Eye Irritation:	0.146
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC96259

Natural Product ID:	NPC96259
*Common Name:**	Tamirin
IUPAC Name:	(3aS,4R,5E,11aS)-4-hydroxy-6-methyl-3,10-dimethylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2,9-dione
Synonyms:	tamirin
Standard InCHIKey:	VHFDUPDINCLGLT-PMDFWAKSSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6,12-14,17H,2-5,7H2,1H3/b8-6+/t12-,13+,14+/m1/s1
SMILES:	C/C/1=C[C@@H](O)[C@H]2[C@H](CC(=C)C(=O)CC1)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL363460
PubChem CID:	10106765
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
NPO26031	Acacia auriculiformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(80)80226-3]
NPO26536	Garcinia humilis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844964]
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558746]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	figs	Tongolo-Yaound, in the Central Region of Cameroon	2008-JUN	PMID[21619045]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	fruit	n.a.	PMID[21619045]
NPO17503	Conospermum incurvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7853001]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26658	Commiphora dalzielii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26536	Garcinia humilis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21612	Anthelia glauca	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21540	Naucleopsis stipularis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17763	Lobularia elongata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13003	Sogatella furcifera	Species	Delphacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26981	Thunbergia laurifolia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19749	Carpolobia glabrescens	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26783	Jurinea eriobasis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20662	Epinephelus drummondhayi	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17503	Conospermum incurvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21134	Thaumetopoea pityocampa	Species	0todontidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18806	Neodilsea yendoana	Species	Dumontiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21673	Lupinus caudatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20469	Acer caesium	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26431	Aplophyllum sieversii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26379	Metrosideros umbellata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3030	Chaenorhinum villosum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21224	Rubus pinfaensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16895	Croton sarcopetalus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20044	Schistostephium crataegifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20925	Fusarium culmorum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21000	Elysia halimedae	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19608	Aconitum likiangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26031	Acacia auriculiformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26454	Acacia oswaldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1550	Talaromyces purpureogenus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8746	Melaleuca triumphalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19874	Polygonatum glaberrimum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7765	Quercus spicata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11310	Baorangia pseudocalopus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21419	Biscogniauxia mediterranea	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26136	Abuta racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25745	Grindelia arenicola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26268	Salvia aethiopis	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
Others	3

Activity Type	# Activity
Individual Protein	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	50.0	uM	PMID[487080]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.69	n.a.	PMID[487080]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	50.0	uM	PMID[487081]

☑ 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 NPC96259 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	170
0.1-0.2	1065
0.2-0.3	4769
0.3-0.4	11203
0.4-0.5	13633
0.5-0.6	6754
0.6-0.7	3819
0.7-0.8	1050
0.8-0.85	107
0.85-0.9	71
0.9-0.95	44
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141193
0.9747	High Similarity	NPC114979
0.9747	High Similarity	NPC191476
0.9625	High Similarity	NPC255307
0.9615	High Similarity	NPC24417
0.9506	High Similarity	NPC475461
0.9506	High Similarity	NPC305475
0.95	High Similarity	NPC476804
0.9494	High Similarity	NPC229825
0.9383	High Similarity	NPC165162
0.9375	High Similarity	NPC169575
0.9375	High Similarity	NPC131669
0.9375	High Similarity	NPC473390
0.9375	High Similarity	NPC40746
0.9367	High Similarity	NPC52861
0.9359	High Similarity	NPC98557
0.9359	High Similarity	NPC167881
0.9259	High Similarity	NPC158756
0.9231	High Similarity	NPC471465
0.9231	High Similarity	NPC196653
0.9146	High Similarity	NPC470755
0.9136	High Similarity	NPC59097
0.9059	High Similarity	NPC469368
0.9048	High Similarity	NPC476805
0.9048	High Similarity	NPC476803
0.9036	High Similarity	NPC469910
0.9036	High Similarity	NPC150755
0.8974	High Similarity	NPC68819
0.8875	High Similarity	NPC89128
0.8875	High Similarity	NPC270126
0.8861	High Similarity	NPC320630
0.8861	High Similarity	NPC476028
0.8861	High Similarity	NPC7563
0.8861	High Similarity	NPC171204
0.8861	High Similarity	NPC141789
0.8861	High Similarity	NPC116177
0.8851	High Similarity	NPC162205
0.8851	High Similarity	NPC228451
0.8851	High Similarity	NPC273579
0.8851	High Similarity	NPC288240
0.8851	High Similarity	NPC125674
0.8851	High Similarity	NPC295204
0.8851	High Similarity	NPC475838
0.8851	High Similarity	NPC475302
0.8846	High Similarity	NPC155587
0.8837	High Similarity	NPC475855
0.8837	High Similarity	NPC144133
0.8837	High Similarity	NPC179394
0.8837	High Similarity	NPC129419
0.8824	High Similarity	NPC475819
0.8824	High Similarity	NPC473715
0.878	High Similarity	NPC89555
0.875	High Similarity	NPC108816
0.875	High Similarity	NPC93763
0.875	High Similarity	NPC474247
0.875	High Similarity	NPC57405
0.875	High Similarity	NPC303942
0.8734	High Similarity	NPC235906
0.8721	High Similarity	NPC474032
0.8721	High Similarity	NPC268298
0.8675	High Similarity	NPC116543
0.8659	High Similarity	NPC301477
0.8659	High Similarity	NPC25684
0.8659	High Similarity	NPC470241
0.8659	High Similarity	NPC281949
0.8642	High Similarity	NPC470239
0.8642	High Similarity	NPC470244
0.8621	High Similarity	NPC474232
0.8605	High Similarity	NPC136879
0.859	High Similarity	NPC295633
0.859	High Similarity	NPC58956
0.859	High Similarity	NPC269206
0.8556	High Similarity	NPC230800
0.8556	High Similarity	NPC279621
0.8537	High Similarity	NPC281132
0.8523	High Similarity	NPC473321
0.8519	High Similarity	NPC267231
0.8506	High Similarity	NPC206001
0.8506	High Similarity	NPC218927
0.8481	Intermediate Similarity	NPC114727
0.8481	Intermediate Similarity	NPC476590
0.8471	Intermediate Similarity	NPC261380
0.8452	Intermediate Similarity	NPC474703
0.8434	Intermediate Similarity	NPC141810
0.8427	Intermediate Similarity	NPC469645
0.8427	Intermediate Similarity	NPC475912
0.8427	Intermediate Similarity	NPC469692
0.8409	Intermediate Similarity	NPC473619
0.8395	Intermediate Similarity	NPC97516
0.8395	Intermediate Similarity	NPC65603
0.8391	Intermediate Similarity	NPC477302
0.8375	Intermediate Similarity	NPC138408
0.8375	Intermediate Similarity	NPC226669
0.8375	Intermediate Similarity	NPC193351
0.8372	Intermediate Similarity	NPC50637
0.8352	Intermediate Similarity	NPC473859
0.8333	Intermediate Similarity	NPC121825
0.8333	Intermediate Similarity	NPC85772
0.8315	Intermediate Similarity	NPC111114
0.8315	Intermediate Similarity	NPC300312
0.8315	Intermediate Similarity	NPC261607
0.8295	Intermediate Similarity	NPC295312
0.828	Intermediate Similarity	NPC288876
0.8276	Intermediate Similarity	NPC237540
0.8256	Intermediate Similarity	NPC21469
0.825	Intermediate Similarity	NPC140287
0.825	Intermediate Similarity	NPC476355
0.8242	Intermediate Similarity	NPC475659
0.8242	Intermediate Similarity	NPC477922
0.8242	Intermediate Similarity	NPC471142
0.8242	Intermediate Similarity	NPC36954
0.8242	Intermediate Similarity	NPC471141
0.8242	Intermediate Similarity	NPC270013
0.8242	Intermediate Similarity	NPC304886
0.8242	Intermediate Similarity	NPC14961
0.8235	Intermediate Similarity	NPC250315
0.8228	Intermediate Similarity	NPC163003
0.8228	Intermediate Similarity	NPC129665
0.8214	Intermediate Similarity	NPC471325
0.8202	Intermediate Similarity	NPC106510
0.8202	Intermediate Similarity	NPC71533
0.8193	Intermediate Similarity	NPC19841
0.8193	Intermediate Similarity	NPC178277
0.8193	Intermediate Similarity	NPC617
0.8182	Intermediate Similarity	NPC202672
0.8172	Intermediate Similarity	NPC141191
0.8172	Intermediate Similarity	NPC473326
0.8171	Intermediate Similarity	NPC41780
0.8171	Intermediate Similarity	NPC470240
0.8171	Intermediate Similarity	NPC474760
0.8171	Intermediate Similarity	NPC476794
0.8171	Intermediate Similarity	NPC187568
0.8161	Intermediate Similarity	NPC469483
0.8161	Intermediate Similarity	NPC261721
0.8161	Intermediate Similarity	NPC107787
0.8152	Intermediate Similarity	NPC477921
0.8152	Intermediate Similarity	NPC476315
0.814	Intermediate Similarity	NPC165287
0.814	Intermediate Similarity	NPC115786
0.8132	Intermediate Similarity	NPC81386
0.8132	Intermediate Similarity	NPC470010
0.8132	Intermediate Similarity	NPC323008
0.8132	Intermediate Similarity	NPC474035
0.8132	Intermediate Similarity	NPC470013
0.8132	Intermediate Similarity	NPC167219
0.8132	Intermediate Similarity	NPC262133
0.8132	Intermediate Similarity	NPC474338
0.8118	Intermediate Similarity	NPC173609
0.8118	Intermediate Similarity	NPC474252
0.8111	Intermediate Similarity	NPC131209
0.8111	Intermediate Similarity	NPC30515
0.8111	Intermediate Similarity	NPC184463
0.809	Intermediate Similarity	NPC166919
0.8072	Intermediate Similarity	NPC128276
0.8068	Intermediate Similarity	NPC160138
0.8068	Intermediate Similarity	NPC72513
0.8065	Intermediate Similarity	NPC169205
0.8049	Intermediate Similarity	NPC123360
0.8046	Intermediate Similarity	NPC78089
0.8046	Intermediate Similarity	NPC28887
0.8043	Intermediate Similarity	NPC193645
0.8043	Intermediate Similarity	NPC48803
0.8043	Intermediate Similarity	NPC90121
0.8043	Intermediate Similarity	NPC52044
0.8043	Intermediate Similarity	NPC275960
0.8043	Intermediate Similarity	NPC170120
0.8025	Intermediate Similarity	NPC48641
0.8023	Intermediate Similarity	NPC318468
0.8022	Intermediate Similarity	NPC179746
0.8022	Intermediate Similarity	NPC212486
0.8022	Intermediate Similarity	NPC476300
0.8022	Intermediate Similarity	NPC81419
0.8	Intermediate Similarity	NPC473448
0.8	Intermediate Similarity	NPC110443
0.8	Intermediate Similarity	NPC474761
0.8	Intermediate Similarity	NPC128733
0.8	Intermediate Similarity	NPC325031
0.8	Intermediate Similarity	NPC185141
0.8	Intermediate Similarity	NPC51004
0.8	Intermediate Similarity	NPC46998
0.8	Intermediate Similarity	NPC476004
0.8	Intermediate Similarity	NPC164598
0.8	Intermediate Similarity	NPC474339
0.8	Intermediate Similarity	NPC133907
0.7979	Intermediate Similarity	NPC187268
0.7976	Intermediate Similarity	NPC475210
0.7976	Intermediate Similarity	NPC264227
0.7976	Intermediate Similarity	NPC63649
0.7976	Intermediate Similarity	NPC472965
0.7957	Intermediate Similarity	NPC306041
0.7957	Intermediate Similarity	NPC185553
0.7955	Intermediate Similarity	NPC236692
0.7955	Intermediate Similarity	NPC309757
0.7952	Intermediate Similarity	NPC57744
0.7935	Intermediate Similarity	NPC477131
0.7935	Intermediate Similarity	NPC198853
0.7935	Intermediate Similarity	NPC469632
0.7931	Intermediate Similarity	NPC31086
0.7931	Intermediate Similarity	NPC472958
0.7931	Intermediate Similarity	NPC472957

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 NPC96259 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1581
0.2-0.3	3733
0.3-0.4	2469
0.4-0.5	762
0.5-0.6	347
0.6-0.7	77
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8043	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7154	Phase 3
0.7802	Intermediate Similarity	NPD5785	Approved
0.764	Intermediate Similarity	NPD5363	Approved
0.7609	Intermediate Similarity	NPD6698	Approved
0.7609	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD4269	Approved
0.7471	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5362	Discontinued
0.7363	Intermediate Similarity	NPD5786	Approved
0.7312	Intermediate Similarity	NPD1695	Approved
0.7303	Intermediate Similarity	NPD6435	Approved
0.7273	Intermediate Similarity	NPD4821	Approved
0.7273	Intermediate Similarity	NPD4822	Approved
0.7273	Intermediate Similarity	NPD4819	Approved
0.7273	Intermediate Similarity	NPD4252	Approved
0.7273	Intermediate Similarity	NPD4820	Approved
0.7253	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1694	Approved
0.7245	Intermediate Similarity	NPD4225	Approved
0.7241	Intermediate Similarity	NPD4268	Approved
0.7241	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4271	Approved
0.7212	Intermediate Similarity	NPD6371	Approved
0.7191	Intermediate Similarity	NPD5369	Approved
0.7174	Intermediate Similarity	NPD4249	Approved
0.7158	Intermediate Similarity	NPD7983	Approved
0.7097	Intermediate Similarity	NPD4250	Approved
0.7097	Intermediate Similarity	NPD4251	Approved
0.7087	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5368	Approved
0.7053	Intermediate Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5779	Approved
0.6907	Remote Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5331	Approved
0.6848	Remote Similarity	NPD5332	Approved
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4790	Discontinued
0.6774	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5370	Suspended
0.6742	Remote Similarity	NPD4756	Discovery
0.6739	Remote Similarity	NPD5209	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.67	Remote Similarity	NPD7839	Suspended
0.6698	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5282	Discontinued
0.6633	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6101	Approved
0.6517	Remote Similarity	NPD8039	Approved
0.6505	Remote Similarity	NPD7639	Approved
0.6505	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD7637	Suspended
0.6465	Remote Similarity	NPD6411	Approved
0.6455	Remote Similarity	NPD6053	Discontinued
0.6442	Remote Similarity	NPD5344	Discontinued
0.6408	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD7902	Approved
0.6311	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD5697	Approved
0.6293	Remote Similarity	NPD8515	Approved
0.6293	Remote Similarity	NPD8513	Phase 3
0.6293	Remote Similarity	NPD8516	Approved
0.6293	Remote Similarity	NPD8517	Approved
0.6275	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6211	Remote Similarity	NPD3667	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD6648	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.6168	Remote Similarity	NPD6647	Phase 2
0.6163	Remote Similarity	NPD7331	Phase 2
0.6147	Remote Similarity	NPD5701	Approved
0.6145	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7515	Phase 2
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD6422	Discontinued
0.6122	Remote Similarity	NPD7146	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6122	Remote Similarity	NPD3618	Phase 1
0.6118	Remote Similarity	NPD3197	Phase 1
0.6092	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6082	Remote Similarity	NPD4786	Approved
0.6082	Remote Similarity	NPD3133	Approved
0.6082	Remote Similarity	NPD3666	Approved
0.6075	Remote Similarity	NPD5211	Phase 2
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD368	Approved
0.6036	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8074	Phase 3
0.602	Remote Similarity	NPD1696	Phase 3
0.6019	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7900	Approved
0.6018	Remote Similarity	NPD8297	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.5982	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5693	Phase 1
0.598	Remote Similarity	NPD5284	Approved
0.598	Remote Similarity	NPD5281	Approved
0.5979	Remote Similarity	NPD6110	Phase 1
0.5977	Remote Similarity	NPD3704	Approved
0.5963	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD5210	Approved
0.596	Remote Similarity	NPD5279	Phase 3
0.5941	Remote Similarity	NPD4753	Phase 2
0.5926	Remote Similarity	NPD7632	Discontinued
0.5918	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7642	Approved
0.5909	Remote Similarity	NPD6008	Approved
0.5905	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7641	Discontinued
0.5888	Remote Similarity	NPD5285	Approved
0.5888	Remote Similarity	NPD5286	Approved
0.5888	Remote Similarity	NPD4696	Approved
0.5875	Remote Similarity	NPD3172	Approved
0.5862	Remote Similarity	NPD7341	Phase 2
0.5862	Remote Similarity	NPD6274	Approved
0.5856	Remote Similarity	NPD6412	Phase 2
0.5849	Remote Similarity	NPD4755	Approved
0.5841	Remote Similarity	NPD2067	Discontinued
0.5833	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD8035	Phase 2
0.5825	Remote Similarity	NPD8034	Phase 2
0.5825	Remote Similarity	NPD6079	Approved
0.5816	Remote Similarity	NPD6695	Phase 3
0.5812	Remote Similarity	NPD7500	Approved
0.581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3194	Approved
0.5802	Remote Similarity	NPD3195	Phase 2
0.5802	Remote Similarity	NPD3196	Approved
0.5802	Remote Similarity	NPD4266	Approved
0.58	Remote Similarity	NPD4519	Discontinued
0.58	Remote Similarity	NPD4623	Approved
0.5789	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3732	Approved
0.5785	Remote Similarity	NPD7829	Approved
0.5785	Remote Similarity	NPD7830	Approved
0.5784	Remote Similarity	NPD5328	Approved
0.578	Remote Similarity	NPD5224	Approved
0.578	Remote Similarity	NPD5225	Approved
0.578	Remote Similarity	NPD5226	Approved
0.578	Remote Similarity	NPD4633	Approved
0.5769	Remote Similarity	NPD4202	Approved
0.5758	Remote Similarity	NPD3668	Phase 3
0.5755	Remote Similarity	NPD4697	Phase 3
0.5755	Remote Similarity	NPD5222	Approved
0.5755	Remote Similarity	NPD5221	Approved
0.5755	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6413	Approved
0.575	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8444	Approved
0.5741	Remote Similarity	NPD4700	Approved
0.5732	Remote Similarity	NPD342	Phase 1
0.5728	Remote Similarity	NPD5207	Approved
0.5727	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5175	Approved
0.5727	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7260	Phase 2

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