NPASS Compound

Structure

CID218927 OpenBabel06191716012D 22 23 0 0 1 0 0 0 0 0999 V2000 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 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 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 9 1 1 6 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 8 1 1 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 15 11 1 1 0 0 0 15 16 1 0 0 0 0 16 19 1 1 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	318.881
LogP:	1.784
LogD:	1.378
LogS:	-2.338
# Rotatable Bonds:	6
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	4.31
Fsp3:	0.647
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:	-4.704
MDCK Permeability:	7.494530291296542e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.133
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.776

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.59
Plasma Protein Binding (PPB):	71.47249603271484%
Volume Distribution (VD):	1.433
Pgp-substrate:	27.531105041503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.194
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.307
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.366
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	7.135
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.626
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.698
Maximum Recommended Daily Dose:	0.54
Skin Sensitization:	0.585
Carcinogencity:	0.714
Eye Corrosion:	0.016
Eye Irritation:	0.184
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC218927

Natural Product ID:	NPC218927
*Common Name:**	1-O-Acetylbritannilactone
IUPAC Name:	[(4S)-4-[(3aS,4R,7aR)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3a,4,7,7a-tetrahydro-1-benzofuran-5-yl]pentyl] acetate
Synonyms:	1-O-Acetylbritannilactone
Standard InCHIKey:	QKUFZFLZBUSEHN-CIGJXOAISA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-9(6-5-7-21-12(4)18)14-10(2)8-13-15(16(14)19)11(3)17(20)22-13/h9,13,15-16,19H,3,5-8H2,1-2,4H3/t9-,13+,15+,16-/m0/s1
SMILES:	CC(=O)OCCC[C@@H](C1=C(C)C[C@@H]2[C@H]([C@H]1O)C(=C)C(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL274543
PubChem CID:	10063871
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
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27276091]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9124	Inula japonica	Species	Asteraceae	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	4
Others	22

Activity Type	# Activity
Cell Line	26

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	ID50	=	18.4	ug ml-1	PMID[456373]
NPT181	Cell Line	Bel-7402	Homo sapiens	ID50	=	15.6	ug ml-1	PMID[456373]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100000.0	nM	PMID[456374]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	96000.0	nM	PMID[456374]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[456374]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	100000.0	nM	PMID[456374]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	13.44	%	PMID[456374]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	11.32	%	PMID[456374]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	16.48	%	PMID[456374]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	16.59	%	PMID[456374]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	35.79	%	PMID[456374]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	5.36	%	PMID[456374]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	6.81	%	PMID[456374]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	11.68	%	PMID[456374]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	9.26	%	PMID[456374]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	14.87	%	PMID[456374]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	4.05	%	PMID[456374]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	7.26	%	PMID[456374]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	4.37	%	PMID[456374]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	5.69	%	PMID[456374]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	22.19	%	PMID[456374]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	15.37	%	PMID[456374]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	17.28	%	PMID[456374]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	14.67	%	PMID[456374]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	14.84	%	PMID[456374]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	18.85	%	PMID[456374]

☑ 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 NPC218927 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	163
0.1-0.2	1045
0.2-0.3	4338
0.3-0.4	10536
0.4-0.5	12978
0.5-0.6	7090
0.6-0.7	4775
0.7-0.8	1534
0.8-0.85	149
0.85-0.9	68
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC206001
0.988	High Similarity	NPC136879
0.988	High Similarity	NPC477302
0.9398	High Similarity	NPC159635
0.8837	High Similarity	NPC255307
0.875	High Similarity	NPC277771
0.8736	High Similarity	NPC305475
0.8736	High Similarity	NPC475461
0.8721	High Similarity	NPC114979
0.8721	High Similarity	NPC191476
0.8667	High Similarity	NPC186363
0.8667	High Similarity	NPC233345
0.8621	High Similarity	NPC165162
0.8605	High Similarity	NPC473390
0.8605	High Similarity	NPC131669
0.8587	High Similarity	NPC183012
0.8511	High Similarity	NPC216478
0.8506	High Similarity	NPC96259
0.8506	High Similarity	NPC476804
0.8506	High Similarity	NPC295799
0.8506	High Similarity	NPC141193
0.8488	Intermediate Similarity	NPC229825
0.8391	Intermediate Similarity	NPC169575
0.8391	Intermediate Similarity	NPC40746
0.8372	Intermediate Similarity	NPC24417
0.8352	Intermediate Similarity	NPC469368
0.8333	Intermediate Similarity	NPC7563
0.8333	Intermediate Similarity	NPC320630
0.8333	Intermediate Similarity	NPC116177
0.8315	Intermediate Similarity	NPC150755
0.8315	Intermediate Similarity	NPC250981
0.8298	Intermediate Similarity	NPC284518
0.8295	Intermediate Similarity	NPC158756
0.828	Intermediate Similarity	NPC24861
0.8276	Intermediate Similarity	NPC89555
0.8261	Intermediate Similarity	NPC72845
0.8235	Intermediate Similarity	NPC108816
0.8235	Intermediate Similarity	NPC93763
0.8229	Intermediate Similarity	NPC47024
0.8229	Intermediate Similarity	NPC476299
0.8229	Intermediate Similarity	NPC474012
0.8222	Intermediate Similarity	NPC181103
0.8222	Intermediate Similarity	NPC470012
0.8222	Intermediate Similarity	NPC312561
0.8222	Intermediate Similarity	NPC305029
0.8211	Intermediate Similarity	NPC474343
0.8202	Intermediate Similarity	NPC470755
0.8191	Intermediate Similarity	NPC157686
0.8191	Intermediate Similarity	NPC259042
0.8172	Intermediate Similarity	NPC228451
0.8172	Intermediate Similarity	NPC475912
0.8172	Intermediate Similarity	NPC125674
0.8172	Intermediate Similarity	NPC139692
0.8172	Intermediate Similarity	NPC475838
0.8163	Intermediate Similarity	NPC476237
0.8161	Intermediate Similarity	NPC281949
0.8161	Intermediate Similarity	NPC52861
0.8161	Intermediate Similarity	NPC25684
0.8161	Intermediate Similarity	NPC141810
0.8161	Intermediate Similarity	NPC301477
0.8152	Intermediate Similarity	NPC232426
0.8152	Intermediate Similarity	NPC281942
0.8152	Intermediate Similarity	NPC158488
0.8152	Intermediate Similarity	NPC129419
0.8152	Intermediate Similarity	NPC475855
0.8144	Intermediate Similarity	NPC244456
0.8144	Intermediate Similarity	NPC469657
0.8144	Intermediate Similarity	NPC81530
0.814	Intermediate Similarity	NPC167881
0.814	Intermediate Similarity	NPC98557
0.814	Intermediate Similarity	NPC470244
0.814	Intermediate Similarity	NPC470239
0.8132	Intermediate Similarity	NPC477128
0.8132	Intermediate Similarity	NPC476805
0.8132	Intermediate Similarity	NPC476803
0.8111	Intermediate Similarity	NPC185638
0.8111	Intermediate Similarity	NPC85698
0.8111	Intermediate Similarity	NPC469910
0.8111	Intermediate Similarity	NPC477920
0.8111	Intermediate Similarity	NPC6979
0.8111	Intermediate Similarity	NPC473226
0.8105	Intermediate Similarity	NPC242848
0.8105	Intermediate Similarity	NPC234993
0.8105	Intermediate Similarity	NPC134072
0.8085	Intermediate Similarity	NPC477129
0.8085	Intermediate Similarity	NPC57117
0.8085	Intermediate Similarity	NPC225474
0.8085	Intermediate Similarity	NPC477130
0.8085	Intermediate Similarity	NPC469596
0.8085	Intermediate Similarity	NPC148000
0.8085	Intermediate Similarity	NPC474247
0.8068	Intermediate Similarity	NPC474252
0.8065	Intermediate Similarity	NPC141831
0.8061	Intermediate Similarity	NPC273005
0.8061	Intermediate Similarity	NPC136289
0.8061	Intermediate Similarity	NPC476081
0.8061	Intermediate Similarity	NPC31058
0.8061	Intermediate Similarity	NPC469606
0.8043	Intermediate Similarity	NPC268298
0.8043	Intermediate Similarity	NPC295312
0.8043	Intermediate Similarity	NPC50488
0.8043	Intermediate Similarity	NPC474396
0.8043	Intermediate Similarity	NPC168131
0.8023	Intermediate Similarity	NPC471465
0.8023	Intermediate Similarity	NPC196653
0.8023	Intermediate Similarity	NPC267231
0.8021	Intermediate Similarity	NPC70145
0.8021	Intermediate Similarity	NPC224356
0.8021	Intermediate Similarity	NPC132753
0.8021	Intermediate Similarity	NPC91695
0.8021	Intermediate Similarity	NPC175351
0.8021	Intermediate Similarity	NPC473963
0.8021	Intermediate Similarity	NPC121402
0.8021	Intermediate Similarity	NPC151681
0.802	Intermediate Similarity	NPC189075
0.802	Intermediate Similarity	NPC275539
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC469607
0.8	Intermediate Similarity	NPC36954
0.8	Intermediate Similarity	NPC52628
0.8	Intermediate Similarity	NPC477125
0.8	Intermediate Similarity	NPC270013
0.8	Intermediate Similarity	NPC304886
0.798	Intermediate Similarity	NPC159533
0.7979	Intermediate Similarity	NPC115021
0.7979	Intermediate Similarity	NPC469645
0.7979	Intermediate Similarity	NPC469692
0.7979	Intermediate Similarity	NPC475302
0.7978	Intermediate Similarity	NPC250315
0.7978	Intermediate Similarity	NPC59097
0.7959	Intermediate Similarity	NPC308824
0.7957	Intermediate Similarity	NPC179394
0.7957	Intermediate Similarity	NPC144133
0.7955	Intermediate Similarity	NPC470241
0.7938	Intermediate Similarity	NPC23364
0.7938	Intermediate Similarity	NPC316598
0.7938	Intermediate Similarity	NPC278386
0.7938	Intermediate Similarity	NPC478056
0.7938	Intermediate Similarity	NPC124512
0.7938	Intermediate Similarity	NPC159763
0.7935	Intermediate Similarity	NPC202672
0.7935	Intermediate Similarity	NPC475819
0.7931	Intermediate Similarity	NPC617
0.7931	Intermediate Similarity	NPC89128
0.7931	Intermediate Similarity	NPC19841
0.7921	Intermediate Similarity	NPC143609
0.7921	Intermediate Similarity	NPC110496
0.7921	Intermediate Similarity	NPC187435
0.7921	Intermediate Similarity	NPC67321
0.7917	Intermediate Similarity	NPC279621
0.7917	Intermediate Similarity	NPC154526
0.7917	Intermediate Similarity	NPC476315
0.7917	Intermediate Similarity	NPC472363
0.7917	Intermediate Similarity	NPC202833
0.7917	Intermediate Similarity	NPC472362
0.7917	Intermediate Similarity	NPC93245
0.7917	Intermediate Similarity	NPC230800
0.7917	Intermediate Similarity	NPC473964
0.7912	Intermediate Similarity	NPC329692
0.7912	Intermediate Similarity	NPC9231
0.7907	Intermediate Similarity	NPC187568
0.7907	Intermediate Similarity	NPC97516
0.7907	Intermediate Similarity	NPC141789
0.7907	Intermediate Similarity	NPC41780
0.7907	Intermediate Similarity	NPC171204
0.7907	Intermediate Similarity	NPC476794
0.7907	Intermediate Similarity	NPC476028
0.7907	Intermediate Similarity	NPC470240
0.79	Intermediate Similarity	NPC146731
0.79	Intermediate Similarity	NPC296950
0.79	Intermediate Similarity	NPC118911
0.7895	Intermediate Similarity	NPC121825
0.7895	Intermediate Similarity	NPC470697
0.7895	Intermediate Similarity	NPC250075
0.7895	Intermediate Similarity	NPC474035
0.7895	Intermediate Similarity	NPC474338
0.7895	Intermediate Similarity	NPC81386
0.7895	Intermediate Similarity	NPC53685
0.7889	Intermediate Similarity	NPC470011
0.7889	Intermediate Similarity	NPC472326
0.7879	Intermediate Similarity	NPC58329
0.7879	Intermediate Similarity	NPC137430
0.7879	Intermediate Similarity	NPC39996
0.7879	Intermediate Similarity	NPC164551
0.7879	Intermediate Similarity	NPC295791
0.7879	Intermediate Similarity	NPC165250
0.7872	Intermediate Similarity	NPC30515
0.7872	Intermediate Similarity	NPC184463
0.7872	Intermediate Similarity	NPC252433
0.7865	Intermediate Similarity	NPC178676
0.7864	Intermediate Similarity	NPC5103
0.7857	Intermediate Similarity	NPC476303
0.7857	Intermediate Similarity	NPC476274
0.7849	Intermediate Similarity	NPC5509
0.7849	Intermediate Similarity	NPC73995
0.7849	Intermediate Similarity	NPC194642
0.7849	Intermediate Similarity	NPC474032
0.7849	Intermediate Similarity	NPC116620
0.7835	Intermediate Similarity	NPC136781
0.7835	Intermediate Similarity	NPC254496

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 NPC218927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1540
0.2-0.3	3621
0.3-0.4	2513
0.4-0.5	828
0.5-0.6	349
0.6-0.7	117
0.7-0.8	29
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
0.7938	Intermediate Similarity	NPD4225	Approved
0.7609	Intermediate Similarity	NPD1694	Approved
0.7449	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7115	Discovery
0.7396	Intermediate Similarity	NPD6698	Approved
0.7396	Intermediate Similarity	NPD46	Approved
0.7391	Intermediate Similarity	NPD7154	Phase 3
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD6399	Phase 3
0.7245	Intermediate Similarity	NPD5779	Approved
0.7245	Intermediate Similarity	NPD5778	Approved
0.7228	Intermediate Similarity	NPD7638	Approved
0.7216	Intermediate Similarity	NPD5785	Approved
0.7129	Intermediate Similarity	NPD7902	Approved
0.7103	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5697	Approved
0.7065	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5363	Approved
0.7037	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5362	Discontinued
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6981	Remote Similarity	NPD7128	Approved
0.6981	Remote Similarity	NPD6675	Approved
0.6981	Remote Similarity	NPD6402	Approved
0.6981	Remote Similarity	NPD5739	Approved
0.6979	Remote Similarity	NPD3618	Phase 1
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD7515	Phase 2
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6372	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6939	Remote Similarity	NPD6101	Approved
0.6939	Remote Similarity	NPD1695	Approved
0.6939	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5344	Discontinued
0.6916	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD4269	Approved
0.6915	Remote Similarity	NPD4270	Approved
0.6909	Remote Similarity	NPD6053	Discontinued
0.6882	Remote Similarity	NPD4822	Approved
0.6882	Remote Similarity	NPD4819	Approved
0.6882	Remote Similarity	NPD4821	Approved
0.6882	Remote Similarity	NPD4820	Approved
0.6881	Remote Similarity	NPD6371	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD7102	Approved
0.6875	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8516	Approved
0.687	Remote Similarity	NPD8517	Approved
0.687	Remote Similarity	NPD8513	Phase 3
0.687	Remote Similarity	NPD8515	Approved
0.6869	Remote Similarity	NPD7838	Discovery
0.6857	Remote Similarity	NPD7632	Discontinued
0.6857	Remote Similarity	NPD5211	Phase 2
0.6852	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6852	Remote Similarity	NPD7320	Approved
0.6848	Remote Similarity	NPD4271	Approved
0.6848	Remote Similarity	NPD4268	Approved
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6804	Remote Similarity	NPD5786	Approved
0.6804	Remote Similarity	NPD4249	Approved
0.68	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD8035	Phase 2
0.68	Remote Similarity	NPD7983	Approved
0.6771	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8297	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6737	Remote Similarity	NPD3667	Approved
0.6737	Remote Similarity	NPD6435	Approved
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6731	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5141	Approved
0.6702	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4696	Approved
0.6635	Remote Similarity	NPD4755	Approved
0.6635	Remote Similarity	NPD6084	Phase 2
0.6635	Remote Similarity	NPD6083	Phase 2
0.6634	Remote Similarity	NPD6079	Approved
0.6632	Remote Similarity	NPD5369	Approved
0.6602	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD5328	Approved
0.6598	Remote Similarity	NPD4786	Approved
0.6583	Remote Similarity	NPD8074	Phase 3
0.6579	Remote Similarity	NPD6274	Approved
0.6571	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD4202	Approved
0.6559	Remote Similarity	NPD4756	Discovery
0.6542	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD5224	Approved
0.6542	Remote Similarity	NPD5225	Approved
0.6542	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD4697	Phase 3
0.6538	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5222	Approved
0.6538	Remote Similarity	NPD5221	Approved
0.6538	Remote Similarity	NPD7839	Suspended
0.6531	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5368	Approved
0.6522	Remote Similarity	NPD8039	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD5331	Approved
0.6495	Remote Similarity	NPD5332	Approved
0.6481	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD5173	Approved
0.6465	Remote Similarity	NPD7146	Approved
0.6465	Remote Similarity	NPD6684	Approved
0.6465	Remote Similarity	NPD5330	Approved
0.6465	Remote Similarity	NPD7521	Approved
0.6465	Remote Similarity	NPD7334	Approved
0.6465	Remote Similarity	NPD6409	Approved
0.6458	Remote Similarity	NPD4790	Discontinued
0.6449	Remote Similarity	NPD5223	Approved
0.6442	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD3133	Approved
0.6429	Remote Similarity	NPD3666	Approved
0.641	Remote Similarity	NPD7101	Approved
0.641	Remote Similarity	NPD7100	Approved
0.6404	Remote Similarity	NPD4632	Approved
0.64	Remote Similarity	NPD3573	Approved
0.6379	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD1696	Phase 3
0.6364	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6339	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD5737	Approved
0.6337	Remote Similarity	NPD6672	Approved
0.6337	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6314	Approved
0.6325	Remote Similarity	NPD6335	Approved
0.6325	Remote Similarity	NPD6313	Approved
0.6311	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD5284	Approved
0.6311	Remote Similarity	NPD5693	Phase 1
0.63	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6868	Approved
0.6286	Remote Similarity	NPD5210	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.6279	Remote Similarity	NPD368	Approved
0.6275	Remote Similarity	NPD5370	Suspended
0.6275	Remote Similarity	NPD4753	Phase 2
0.6263	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.623	Remote Similarity	NPD6616	Approved
0.6224	Remote Similarity	NPD5209	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6216	Remote Similarity	NPD4768	Approved
0.6216	Remote Similarity	NPD4767	Approved
0.621	Remote Similarity	NPD7319	Approved
0.619	Remote Similarity	NPD6001	Approved
0.6186	Remote Similarity	NPD4695	Discontinued
0.6182	Remote Similarity	NPD4754	Approved
0.6179	Remote Similarity	NPD7078	Approved
0.6167	Remote Similarity	NPD6015	Approved
0.6167	Remote Similarity	NPD6908	Approved
0.6167	Remote Similarity	NPD6016	Approved
0.6167	Remote Similarity	NPD5983	Phase 2
0.6167	Remote Similarity	NPD6909	Approved
0.6161	Remote Similarity	NPD6412	Phase 2
0.614	Remote Similarity	NPD5251	Approved
0.614	Remote Similarity	NPD5247	Approved
0.614	Remote Similarity	NPD5249	Phase 3

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