NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	278.135
LogP:	1.097
LogD:	1.021
LogS:	-1.804
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	4.439
Fsp3:	0.667
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:	-4.822
MDCK Permeability:	3.4840373700717464e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.228
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.538
Plasma Protein Binding (PPB):	66.90351104736328%
Volume Distribution (VD):	1.162
Pgp-substrate:	23.851091384887695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	8.834
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.477
Skin Sensitization:	0.476
Carcinogencity:	0.865
Eye Corrosion:	0.029
Eye Irritation:	0.42
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC136879

Natural Product ID:	NPC136879
*Common Name:**	Britannilactone
IUPAC Name:	(3aS,4R,7aR)-4-hydroxy-5-[(2S)-5-hydroxypentan-2-yl]-6-methyl-3-methylidene-3a,4,7,7a-tetrahydro-1-benzofuran-2-one
Synonyms:	Britannilactone
Standard InCHIKey:	ASZIGQFYGXSPCO-RHBIEUIISA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-8(5-4-6-16)12-9(2)7-11-13(14(12)17)10(3)15(18)19-11/h8,11,13-14,16-17H,3-7H2,1-2H3/t8-,11+,13+,14-/m0/s1
SMILES:	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:	CHEMBL480648
PubChem CID:	44575246
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	20

Activity Type	# Activity
Cell Line	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	100000.0	nM	PMID[542294]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[542294]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[542294]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	100000.0	nM	PMID[542294]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	11.9	%	PMID[542294]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	12.28	%	PMID[542294]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	12.79	%	PMID[542294]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	15.54	%	PMID[542294]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	28.31	%	PMID[542294]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	5.75	%	PMID[542294]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	6.16	%	PMID[542294]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	6.49	%	PMID[542294]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	6.59	%	PMID[542294]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	7.55	%	PMID[542294]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	7.22	%	PMID[542294]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	5.64	%	PMID[542294]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	5.24	%	PMID[542294]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	8.01	%	PMID[542294]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	12.83	%	PMID[542294]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	7.93	%	PMID[542294]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	10.37	%	PMID[542294]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	10.16	%	PMID[542294]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	8.97	%	PMID[542294]

☑ 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 NPC136879 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	161
0.1-0.2	1036
0.2-0.3	4404
0.3-0.4	10482
0.4-0.5	13401
0.5-0.6	7114
0.6-0.7	4529
0.7-0.8	1349
0.8-0.85	144
0.85-0.9	57
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC206001
0.988	High Similarity	NPC218927
0.9759	High Similarity	NPC477302
0.9277	High Similarity	NPC159635
0.8851	High Similarity	NPC277771
0.8824	High Similarity	NPC114979
0.8824	High Similarity	NPC191476
0.8764	High Similarity	NPC186363
0.8764	High Similarity	NPC233345
0.8721	High Similarity	NPC255307
0.8721	High Similarity	NPC165162
0.8681	High Similarity	NPC183012
0.8621	High Similarity	NPC475461
0.8621	High Similarity	NPC305475
0.8605	High Similarity	NPC96259
0.8605	High Similarity	NPC141193
0.8602	High Similarity	NPC216478
0.8588	High Similarity	NPC229825
0.8488	Intermediate Similarity	NPC131669
0.8488	Intermediate Similarity	NPC473390
0.8471	Intermediate Similarity	NPC24417
0.8409	Intermediate Similarity	NPC250981
0.8391	Intermediate Similarity	NPC295799
0.8391	Intermediate Similarity	NPC476804
0.8372	Intermediate Similarity	NPC89555
0.837	Intermediate Similarity	NPC24861
0.8315	Intermediate Similarity	NPC181103
0.8315	Intermediate Similarity	NPC305029
0.8276	Intermediate Similarity	NPC40746
0.8276	Intermediate Similarity	NPC169575
0.8256	Intermediate Similarity	NPC52861
0.8242	Intermediate Similarity	NPC129419
0.8242	Intermediate Similarity	NPC158488
0.8242	Intermediate Similarity	NPC469368
0.8235	Intermediate Similarity	NPC470244
0.8235	Intermediate Similarity	NPC98557
0.8235	Intermediate Similarity	NPC167881
0.8235	Intermediate Similarity	NPC470239
0.8214	Intermediate Similarity	NPC116177
0.8214	Intermediate Similarity	NPC320630
0.8214	Intermediate Similarity	NPC7563
0.8202	Intermediate Similarity	NPC477920
0.8202	Intermediate Similarity	NPC150755
0.8202	Intermediate Similarity	NPC6979
0.8202	Intermediate Similarity	NPC85698
0.8191	Intermediate Similarity	NPC284518
0.8182	Intermediate Similarity	NPC158756
0.8172	Intermediate Similarity	NPC469596
0.8172	Intermediate Similarity	NPC148000
0.8172	Intermediate Similarity	NPC225474
0.8152	Intermediate Similarity	NPC72845
0.8132	Intermediate Similarity	NPC168131
0.8132	Intermediate Similarity	NPC268298
0.8125	Intermediate Similarity	NPC474012
0.8125	Intermediate Similarity	NPC47024
0.8125	Intermediate Similarity	NPC476299
0.8118	Intermediate Similarity	NPC471465
0.8118	Intermediate Similarity	NPC108816
0.8118	Intermediate Similarity	NPC93763
0.8118	Intermediate Similarity	NPC196653
0.8111	Intermediate Similarity	NPC470012
0.8111	Intermediate Similarity	NPC312561
0.8105	Intermediate Similarity	NPC474343
0.8105	Intermediate Similarity	NPC70145
0.8105	Intermediate Similarity	NPC91695
0.809	Intermediate Similarity	NPC470755
0.809	Intermediate Similarity	NPC52628
0.8085	Intermediate Similarity	NPC259042
0.8085	Intermediate Similarity	NPC157686
0.8068	Intermediate Similarity	NPC59097
0.8065	Intermediate Similarity	NPC125674
0.8065	Intermediate Similarity	NPC475838
0.8065	Intermediate Similarity	NPC139692
0.8065	Intermediate Similarity	NPC228451
0.8065	Intermediate Similarity	NPC475912
0.8061	Intermediate Similarity	NPC476237
0.8046	Intermediate Similarity	NPC25684
0.8046	Intermediate Similarity	NPC301477
0.8046	Intermediate Similarity	NPC470241
0.8046	Intermediate Similarity	NPC141810
0.8046	Intermediate Similarity	NPC281949
0.8043	Intermediate Similarity	NPC232426
0.8043	Intermediate Similarity	NPC475855
0.8043	Intermediate Similarity	NPC281942
0.8041	Intermediate Similarity	NPC469657
0.8041	Intermediate Similarity	NPC81530
0.8041	Intermediate Similarity	NPC244456
0.8023	Intermediate Similarity	NPC89128
0.8022	Intermediate Similarity	NPC476805
0.8022	Intermediate Similarity	NPC477128
0.8022	Intermediate Similarity	NPC476803
0.8021	Intermediate Similarity	NPC23364
0.8	Intermediate Similarity	NPC185638
0.8	Intermediate Similarity	NPC469910
0.8	Intermediate Similarity	NPC134072
0.8	Intermediate Similarity	NPC234993
0.8	Intermediate Similarity	NPC41780
0.8	Intermediate Similarity	NPC242848
0.8	Intermediate Similarity	NPC187568
0.8	Intermediate Similarity	NPC93245
0.8	Intermediate Similarity	NPC9231
0.8	Intermediate Similarity	NPC473226
0.798	Intermediate Similarity	NPC296950
0.7979	Intermediate Similarity	NPC477129
0.7979	Intermediate Similarity	NPC477130
0.7979	Intermediate Similarity	NPC250075
0.7979	Intermediate Similarity	NPC474247
0.7979	Intermediate Similarity	NPC57117
0.7978	Intermediate Similarity	NPC472326
0.7959	Intermediate Similarity	NPC136289
0.7959	Intermediate Similarity	NPC476081
0.7959	Intermediate Similarity	NPC469606
0.7959	Intermediate Similarity	NPC31058
0.7959	Intermediate Similarity	NPC273005
0.7959	Intermediate Similarity	NPC58329
0.7957	Intermediate Similarity	NPC141831
0.7957	Intermediate Similarity	NPC252433
0.7955	Intermediate Similarity	NPC178676
0.7955	Intermediate Similarity	NPC474252
0.7935	Intermediate Similarity	NPC474396
0.7935	Intermediate Similarity	NPC116620
0.7935	Intermediate Similarity	NPC194642
0.7935	Intermediate Similarity	NPC73995
0.7935	Intermediate Similarity	NPC50488
0.7935	Intermediate Similarity	NPC295312
0.7921	Intermediate Similarity	NPC275539
0.7921	Intermediate Similarity	NPC189075
0.7917	Intermediate Similarity	NPC151681
0.7917	Intermediate Similarity	NPC136781
0.7917	Intermediate Similarity	NPC121402
0.7917	Intermediate Similarity	NPC224356
0.7917	Intermediate Similarity	NPC473963
0.7917	Intermediate Similarity	NPC132753
0.7917	Intermediate Similarity	NPC175351
0.7907	Intermediate Similarity	NPC267231
0.79	Intermediate Similarity	NPC477125
0.79	Intermediate Similarity	NPC469607
0.7895	Intermediate Similarity	NPC14961
0.7895	Intermediate Similarity	NPC36954
0.7895	Intermediate Similarity	NPC170120
0.7895	Intermediate Similarity	NPC316215
0.7895	Intermediate Similarity	NPC270013
0.7895	Intermediate Similarity	NPC304886
0.7882	Intermediate Similarity	NPC68819
0.7882	Intermediate Similarity	NPC235906
0.7879	Intermediate Similarity	NPC159533
0.7872	Intermediate Similarity	NPC469645
0.7872	Intermediate Similarity	NPC469692
0.7872	Intermediate Similarity	NPC166346
0.7872	Intermediate Similarity	NPC115021
0.7872	Intermediate Similarity	NPC475302
0.7865	Intermediate Similarity	NPC470948
0.7865	Intermediate Similarity	NPC250315
0.7857	Intermediate Similarity	NPC308824
0.7849	Intermediate Similarity	NPC144133
0.7849	Intermediate Similarity	NPC152467
0.7849	Intermediate Similarity	NPC153853
0.7849	Intermediate Similarity	NPC179394
0.7835	Intermediate Similarity	NPC316598
0.7835	Intermediate Similarity	NPC478056
0.7835	Intermediate Similarity	NPC278386
0.7835	Intermediate Similarity	NPC159763
0.7835	Intermediate Similarity	NPC124512
0.7826	Intermediate Similarity	NPC215831
0.7826	Intermediate Similarity	NPC475819
0.7826	Intermediate Similarity	NPC473715
0.7826	Intermediate Similarity	NPC202672
0.7822	Intermediate Similarity	NPC187435
0.7822	Intermediate Similarity	NPC143609
0.7822	Intermediate Similarity	NPC110496
0.7822	Intermediate Similarity	NPC67321
0.7816	Intermediate Similarity	NPC617
0.7816	Intermediate Similarity	NPC19841
0.7816	Intermediate Similarity	NPC475210
0.7812	Intermediate Similarity	NPC473964
0.7812	Intermediate Similarity	NPC476315
0.7812	Intermediate Similarity	NPC165528
0.7812	Intermediate Similarity	NPC230800
0.7812	Intermediate Similarity	NPC202833
0.7812	Intermediate Similarity	NPC279621
0.7812	Intermediate Similarity	NPC154526
0.7812	Intermediate Similarity	NPC472362
0.7812	Intermediate Similarity	NPC228766
0.7812	Intermediate Similarity	NPC472363
0.7802	Intermediate Similarity	NPC329692
0.78	Intermediate Similarity	NPC146731
0.78	Intermediate Similarity	NPC118911
0.78	Intermediate Similarity	NPC258532
0.7791	Intermediate Similarity	NPC97516
0.7791	Intermediate Similarity	NPC470240
0.7791	Intermediate Similarity	NPC476028
0.7791	Intermediate Similarity	NPC171204
0.7791	Intermediate Similarity	NPC141789
0.7791	Intermediate Similarity	NPC65603
0.7791	Intermediate Similarity	NPC476794
0.7789	Intermediate Similarity	NPC474338
0.7789	Intermediate Similarity	NPC470013
0.7789	Intermediate Similarity	NPC57405
0.7789	Intermediate Similarity	NPC81386
0.7789	Intermediate Similarity	NPC121825

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 NPC136879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1522
0.2-0.3	3634
0.3-0.4	2527
0.4-0.5	832
0.5-0.6	358
0.6-0.7	102
0.7-0.8	26
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
0.7835	Intermediate Similarity	NPD4225	Approved
0.7692	Intermediate Similarity	NPD1694	Approved
0.7526	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7115	Discovery
0.7292	Intermediate Similarity	NPD6698	Approved
0.7292	Intermediate Similarity	NPD46	Approved
0.7283	Intermediate Similarity	NPD7154	Phase 3
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD7638	Approved
0.7113	Intermediate Similarity	NPD5785	Approved
0.703	Intermediate Similarity	NPD7902	Approved
0.701	Intermediate Similarity	NPD1695	Approved
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5697	Approved
0.6957	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5363	Approved
0.6947	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6881	Approved
0.6916	Remote Similarity	NPD6899	Approved
0.6915	Remote Similarity	NPD5362	Discontinued
0.69	Remote Similarity	NPD7748	Approved
0.6887	Remote Similarity	NPD6402	Approved
0.6887	Remote Similarity	NPD5739	Approved
0.6887	Remote Similarity	NPD6675	Approved
0.6887	Remote Similarity	NPD7128	Approved
0.6881	Remote Similarity	NPD6649	Approved
0.6881	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.6869	Remote Similarity	NPD7515	Phase 2
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6372	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6837	Remote Similarity	NPD6101	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5344	Discontinued
0.6822	Remote Similarity	NPD5701	Approved
0.6822	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6053	Discontinued
0.6809	Remote Similarity	NPD4269	Approved
0.6809	Remote Similarity	NPD4270	Approved
0.6789	Remote Similarity	NPD7102	Approved
0.6789	Remote Similarity	NPD6371	Approved
0.6789	Remote Similarity	NPD7290	Approved
0.6789	Remote Similarity	NPD6883	Approved
0.6783	Remote Similarity	NPD8517	Approved
0.6783	Remote Similarity	NPD8513	Phase 3
0.6783	Remote Similarity	NPD8515	Approved
0.6783	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD4821	Approved
0.6774	Remote Similarity	NPD4820	Approved
0.6774	Remote Similarity	NPD4822	Approved
0.6774	Remote Similarity	NPD4819	Approved
0.6771	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7838	Discovery
0.6762	Remote Similarity	NPD5211	Phase 2
0.6762	Remote Similarity	NPD7632	Discontinued
0.6759	Remote Similarity	NPD7320	Approved
0.6759	Remote Similarity	NPD6686	Approved
0.6759	Remote Similarity	NPD6011	Approved
0.6739	Remote Similarity	NPD4268	Approved
0.6739	Remote Similarity	NPD4271	Approved
0.6733	Remote Similarity	NPD7900	Approved
0.6733	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6847	Approved
0.6727	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8130	Phase 1
0.6727	Remote Similarity	NPD6869	Approved
0.6701	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD8034	Phase 2
0.67	Remote Similarity	NPD6411	Approved
0.67	Remote Similarity	NPD7983	Approved
0.67	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD5141	Approved
0.6635	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD4251	Approved
0.6632	Remote Similarity	NPD6435	Approved
0.6632	Remote Similarity	NPD3667	Approved
0.6596	Remote Similarity	NPD4252	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD6648	Approved
0.6571	Remote Similarity	NPD5285	Approved
0.6571	Remote Similarity	NPD5286	Approved
0.6571	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4755	Approved
0.6538	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD6084	Phase 2
0.6535	Remote Similarity	NPD6079	Approved
0.6526	Remote Similarity	NPD5369	Approved
0.6505	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD5328	Approved
0.65	Remote Similarity	NPD8074	Phase 3
0.6495	Remote Similarity	NPD4786	Approved
0.6491	Remote Similarity	NPD6274	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6452	Remote Similarity	NPD4756	Discovery
0.6449	Remote Similarity	NPD5225	Approved
0.6449	Remote Similarity	NPD5226	Approved
0.6449	Remote Similarity	NPD5224	Approved
0.6449	Remote Similarity	NPD4633	Approved
0.6442	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4697	Phase 3
0.6442	Remote Similarity	NPD5221	Approved
0.6442	Remote Similarity	NPD5222	Approved
0.6442	Remote Similarity	NPD7839	Suspended
0.6429	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5368	Approved
0.6415	Remote Similarity	NPD4700	Approved
0.6413	Remote Similarity	NPD8039	Approved
0.6408	Remote Similarity	NPD5282	Discontinued
0.6392	Remote Similarity	NPD5332	Approved
0.6392	Remote Similarity	NPD5331	Approved
0.6389	Remote Similarity	NPD5174	Approved
0.6389	Remote Similarity	NPD5175	Approved
0.6381	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6356	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5223	Approved
0.6354	Remote Similarity	NPD4790	Discontinued
0.6353	Remote Similarity	NPD368	Approved
0.6346	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3665	Phase 1
0.6327	Remote Similarity	NPD3666	Approved
0.6327	Remote Similarity	NPD3133	Approved
0.6325	Remote Similarity	NPD7100	Approved
0.6325	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD4632	Approved
0.63	Remote Similarity	NPD3573	Approved
0.6293	Remote Similarity	NPD6317	Approved
0.6281	Remote Similarity	NPD7507	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6313	Approved
0.6239	Remote Similarity	NPD6314	Approved
0.6239	Remote Similarity	NPD6335	Approved
0.6238	Remote Similarity	NPD6903	Approved
0.6238	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6672	Approved
0.6238	Remote Similarity	NPD5737	Approved
0.6214	Remote Similarity	NPD5281	Approved
0.6214	Remote Similarity	NPD5693	Phase 1
0.6214	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7637	Suspended
0.6214	Remote Similarity	NPD5284	Approved
0.6207	Remote Similarity	NPD6868	Approved
0.62	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7492	Approved
0.619	Remote Similarity	NPD4629	Approved
0.619	Remote Similarity	NPD5210	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6176	Remote Similarity	NPD5370	Suspended
0.6162	Remote Similarity	NPD3668	Phase 3
0.6161	Remote Similarity	NPD4729	Approved
0.6161	Remote Similarity	NPD5128	Approved
0.6161	Remote Similarity	NPD4730	Approved
0.6161	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6009	Approved
0.6148	Remote Similarity	NPD6616	Approved
0.6136	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6054	Approved
0.6129	Remote Similarity	NPD7319	Approved
0.6126	Remote Similarity	NPD4768	Approved
0.6126	Remote Similarity	NPD4767	Approved
0.6122	Remote Similarity	NPD5209	Approved
0.6098	Remote Similarity	NPD7078	Approved
0.6095	Remote Similarity	NPD6001	Approved
0.6091	Remote Similarity	NPD4754	Approved
0.6083	Remote Similarity	NPD6908	Approved
0.6083	Remote Similarity	NPD6015	Approved
0.6083	Remote Similarity	NPD5983	Phase 2
0.6083	Remote Similarity	NPD6016	Approved
0.6083	Remote Similarity	NPD6909	Approved
0.6082	Remote Similarity	NPD4695	Discontinued
0.6071	Remote Similarity	NPD6412	Phase 2
0.6053	Remote Similarity	NPD5249	Phase 3
0.6053	Remote Similarity	NPD5248	Approved
0.6053	Remote Similarity	NPD5247	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