NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	313.24
Volume:	349.424
LogP:	6.495
LogD:	5.473
LogS:	-6.104
# Rotatable Bonds:	1
TPSA:	29.43
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	5.32
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.648
MDCK Permeability:	2.5433408154640347e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	53.13431167602539%
Volume Distribution (VD):	1.872
Pgp-substrate:	36.84684753417969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.149
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.254
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.39
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	1.724
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.746
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.126
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.953
Carcinogencity:	0.891
Eye Corrosion:	0.975
Eye Irritation:	0.868
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: NPC138408

Natural Product ID:	NPC138408
*Common Name:**	Tomentosin
IUPAC Name:	(3aR,7S,8aR)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
Synonyms:	Tomentosin
Standard InCHIKey:	AVFIYMSJDDGDBQ-CUOATXAZSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9,13-14H,3-5,7-8H2,1-2H3/t9-,13+,14+/m0/s1
SMILES:	C[C@H]1C[C@@H]2[C@H](CC=C1CCC(=O)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1164483
PubChem CID:	155173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0000502] Xanthanolides

*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]
NPO33493	inula lineariifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515062]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO33441	leucophyta brownii	Species	Asteraceae	Eukaryota	Resinous Exudates	n.a.	n.a.	PMID[26218649]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
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]
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[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]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	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
ED50	1
IC50	10
Others	7

Activity Type	# Activity
Cell Line	8
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9150.0	nM	PMID[529984]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[529985]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7140.0	nM	PMID[529986]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	26600.0	nM	PMID[529988]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	56500.0	nM	PMID[529988]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15700.0	nM	PMID[529988]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7300.0	nM	PMID[529988]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2000.0	nM	PMID[529990]
NPT348	Organism	Myzus persicae	Myzus persicae	ED50	=	31.9	microg/cm2	PMID[529987]
NPT348	Organism	Myzus persicae	Myzus persicae	Inhibition	=	98.0	%	PMID[529987]
NPT348	Organism	Myzus persicae	Myzus persicae	Inhibition	=	48.0	%	PMID[529987]
NPT348	Organism	Myzus persicae	Myzus persicae	Inhibition	=	19.0	%	PMID[529987]
NPT348	Organism	Myzus persicae	Myzus persicae	Inhibition	=	2.0	%	PMID[529987]
NPT348	Organism	Myzus persicae	Myzus persicae	Inhibition	=	35.0	%	PMID[529987]
NPT348	Organism	Myzus persicae	Myzus persicae	Inhibition	=	61.0	%	PMID[529987]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	>	128.0	ug.mL-1	PMID[529989]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	MIC50	=	128.0	ug.mL-1	PMID[529989]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	=	31.6	ug.mL-1	PMID[529989]

☑ 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 NPC138408 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1306
0.2-0.3	6504
0.3-0.4	16063
0.4-0.5	9344
0.5-0.6	6165
0.6-0.7	2477
0.7-0.8	525
0.8-0.85	69
0.85-0.9	32
0.9-0.95	26
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193351
1.0	High Similarity	NPC226669
0.9718	High Similarity	NPC65603
0.9452	High Similarity	NPC264227
0.9452	High Similarity	NPC63649
0.9452	High Similarity	NPC472965
0.9444	High Similarity	NPC470240
0.9444	High Similarity	NPC476794
0.9437	High Similarity	NPC155587
0.9324	High Similarity	NPC302426
0.92	High Similarity	NPC25684
0.92	High Similarity	NPC301477
0.92	High Similarity	NPC281949
0.9189	High Similarity	NPC182550
0.9189	High Similarity	NPC470239
0.9189	High Similarity	NPC470244
0.9054	High Similarity	NPC472960
0.9041	High Similarity	NPC235906
0.9014	High Similarity	NPC163003
0.9	High Similarity	NPC296522
0.9	High Similarity	NPC144511
0.8961	High Similarity	NPC318468
0.8947	High Similarity	NPC10276
0.8947	High Similarity	NPC35089
0.8919	High Similarity	NPC187568
0.8919	High Similarity	NPC41780
0.8889	High Similarity	NPC472956
0.8889	High Similarity	NPC295633
0.8889	High Similarity	NPC58956
0.8889	High Similarity	NPC269206
0.8873	High Similarity	NPC472955
0.8846	High Similarity	NPC115786
0.8816	High Similarity	NPC69271
0.8816	High Similarity	NPC276356
0.8816	High Similarity	NPC74673
0.88	High Similarity	NPC299235
0.8784	High Similarity	NPC472967
0.8784	High Similarity	NPC266159
0.8767	High Similarity	NPC476355
0.8767	High Similarity	NPC140287
0.8734	High Similarity	NPC165162
0.8718	High Similarity	NPC215294
0.8718	High Similarity	NPC39588
0.8684	High Similarity	NPC617
0.8667	High Similarity	NPC15975
0.8667	High Similarity	NPC195785
0.8625	High Similarity	NPC107787
0.859	High Similarity	NPC173609
0.8571	High Similarity	NPC223904
0.8553	High Similarity	NPC128276
0.8533	High Similarity	NPC123360
0.8533	High Similarity	NPC472959
0.85	High Similarity	NPC161957
0.85	High Similarity	NPC33570
0.85	High Similarity	NPC21471
0.85	High Similarity	NPC78089
0.8493	Intermediate Similarity	NPC129665
0.8462	Intermediate Similarity	NPC141810
0.8462	Intermediate Similarity	NPC471325
0.8442	Intermediate Similarity	NPC178277
0.8442	Intermediate Similarity	NPC270126
0.8421	Intermediate Similarity	NPC171204
0.8421	Intermediate Similarity	NPC476028
0.8421	Intermediate Similarity	NPC97516
0.8421	Intermediate Similarity	NPC57744
0.8421	Intermediate Similarity	NPC7563
0.8421	Intermediate Similarity	NPC116177
0.8421	Intermediate Similarity	NPC141789
0.8421	Intermediate Similarity	NPC320630
0.8375	Intermediate Similarity	NPC96259
0.8375	Intermediate Similarity	NPC141193
0.8375	Intermediate Similarity	NPC156485
0.8354	Intermediate Similarity	NPC89555
0.8354	Intermediate Similarity	NPC178676
0.8333	Intermediate Similarity	NPC470256
0.8313	Intermediate Similarity	NPC268298
0.8312	Intermediate Similarity	NPC471465
0.8312	Intermediate Similarity	NPC196653
0.8312	Intermediate Similarity	NPC108816
0.8312	Intermediate Similarity	NPC93763
0.8312	Intermediate Similarity	NPC267231
0.8272	Intermediate Similarity	NPC110405
0.8272	Intermediate Similarity	NPC235792
0.8267	Intermediate Similarity	NPC469643
0.8267	Intermediate Similarity	NPC320537
0.8267	Intermediate Similarity	NPC469641
0.8267	Intermediate Similarity	NPC143979
0.8267	Intermediate Similarity	NPC472966
0.825	Intermediate Similarity	NPC272814
0.8228	Intermediate Similarity	NPC255580
0.8228	Intermediate Similarity	NPC39411
0.8219	Intermediate Similarity	NPC199557
0.8214	Intermediate Similarity	NPC129419
0.8205	Intermediate Similarity	NPC98557
0.8205	Intermediate Similarity	NPC167881
0.8194	Intermediate Similarity	NPC194871
0.8182	Intermediate Similarity	NPC208223
0.8171	Intermediate Similarity	NPC67493
0.8148	Intermediate Similarity	NPC114979
0.8148	Intermediate Similarity	NPC191476
0.8143	Intermediate Similarity	NPC474658
0.8101	Intermediate Similarity	NPC290508
0.8101	Intermediate Similarity	NPC6823
0.8101	Intermediate Similarity	NPC281132
0.8101	Intermediate Similarity	NPC293418
0.8101	Intermediate Similarity	NPC73052
0.8049	Intermediate Similarity	NPC255307
0.8049	Intermediate Similarity	NPC319795
0.8049	Intermediate Similarity	NPC50362
0.8049	Intermediate Similarity	NPC38468
0.8026	Intermediate Similarity	NPC117746
0.8026	Intermediate Similarity	NPC294434
0.8026	Intermediate Similarity	NPC259599
0.8026	Intermediate Similarity	NPC15499
0.8025	Intermediate Similarity	NPC474703
0.8025	Intermediate Similarity	NPC250315
0.8025	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC37607
0.8	Intermediate Similarity	NPC62815
0.8	Intermediate Similarity	NPC42470
0.8	Intermediate Similarity	NPC470241
0.8	Intermediate Similarity	NPC301969
0.8	Intermediate Similarity	NPC24417
0.7976	Intermediate Similarity	NPC215831
0.7976	Intermediate Similarity	NPC91248
0.7976	Intermediate Similarity	NPC224652
0.7975	Intermediate Similarity	NPC89128
0.7975	Intermediate Similarity	NPC469690
0.7952	Intermediate Similarity	NPC150755
0.7952	Intermediate Similarity	NPC284902
0.7952	Intermediate Similarity	NPC475461
0.7952	Intermediate Similarity	NPC305475
0.7952	Intermediate Similarity	NPC279859
0.7952	Intermediate Similarity	NPC38576
0.7952	Intermediate Similarity	NPC50637
0.7949	Intermediate Similarity	NPC474760
0.7927	Intermediate Similarity	NPC472957
0.7927	Intermediate Similarity	NPC472958
0.7927	Intermediate Similarity	NPC476804
0.7927	Intermediate Similarity	NPC165287
0.7927	Intermediate Similarity	NPC159635
0.7922	Intermediate Similarity	NPC244166
0.7922	Intermediate Similarity	NPC324762
0.7907	Intermediate Similarity	NPC123177
0.7907	Intermediate Similarity	NPC150978
0.7907	Intermediate Similarity	NPC70595
0.7907	Intermediate Similarity	NPC74103
0.7901	Intermediate Similarity	NPC229825
0.7882	Intermediate Similarity	NPC4986
0.7882	Intermediate Similarity	NPC73995
0.7857	Intermediate Similarity	NPC231889
0.7857	Intermediate Similarity	NPC475703
0.7857	Intermediate Similarity	NPC237540
0.7848	Intermediate Similarity	NPC471220
0.7838	Intermediate Similarity	NPC218477
0.7831	Intermediate Similarity	NPC215364
0.7831	Intermediate Similarity	NPC177932
0.7821	Intermediate Similarity	NPC473223
0.7805	Intermediate Similarity	NPC40746
0.7805	Intermediate Similarity	NPC193198
0.7805	Intermediate Similarity	NPC473390
0.7805	Intermediate Similarity	NPC59097
0.7805	Intermediate Similarity	NPC169575
0.7805	Intermediate Similarity	NPC131669
0.7805	Intermediate Similarity	NPC170286
0.7805	Intermediate Similarity	NPC54468
0.7805	Intermediate Similarity	NPC22611
0.7791	Intermediate Similarity	NPC469718
0.7791	Intermediate Similarity	NPC152467
0.7791	Intermediate Similarity	NPC329857
0.7791	Intermediate Similarity	NPC251385
0.7791	Intermediate Similarity	NPC253144
0.7791	Intermediate Similarity	NPC49342
0.7778	Intermediate Similarity	NPC52861
0.7778	Intermediate Similarity	NPC325031
0.7778	Intermediate Similarity	NPC47635
0.7778	Intermediate Similarity	NPC38642
0.7765	Intermediate Similarity	NPC202672
0.775	Intermediate Similarity	NPC19841
0.775	Intermediate Similarity	NPC469620
0.7738	Intermediate Similarity	NPC64153
0.7738	Intermediate Similarity	NPC261721
0.7733	Intermediate Similarity	NPC476591
0.7733	Intermediate Similarity	NPC5714
0.7733	Intermediate Similarity	NPC88877
0.7727	Intermediate Similarity	NPC167219
0.7722	Intermediate Similarity	NPC180290
0.7722	Intermediate Similarity	NPC103987
0.7722	Intermediate Similarity	NPC122264
0.7722	Intermediate Similarity	NPC53581
0.7711	Intermediate Similarity	NPC30486
0.7711	Intermediate Similarity	NPC158756
0.7703	Intermediate Similarity	NPC472266
0.7701	Intermediate Similarity	NPC111114
0.7701	Intermediate Similarity	NPC133698
0.7701	Intermediate Similarity	NPC261607
0.7701	Intermediate Similarity	NPC284185
0.7701	Intermediate Similarity	NPC300312
0.7701	Intermediate Similarity	NPC131209
0.7701	Intermediate Similarity	NPC20713

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 NPC138408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1845
0.2-0.3	4082
0.3-0.4	2084
0.4-0.5	643
0.5-0.6	264
0.6-0.7	47
0.7-0.8	11
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
0.8049	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1695	Approved
0.7831	Intermediate Similarity	NPD1694	Approved
0.764	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5785	Approved
0.7059	Intermediate Similarity	NPD5209	Approved
0.7037	Intermediate Similarity	NPD8039	Approved
0.7011	Intermediate Similarity	NPD5363	Approved
0.6977	Remote Similarity	NPD7154	Phase 3
0.6941	Remote Similarity	NPD5369	Approved
0.686	Remote Similarity	NPD4270	Approved
0.686	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD46	Approved
0.6813	Remote Similarity	NPD6698	Approved
0.6782	Remote Similarity	NPD5362	Discontinued
0.6742	Remote Similarity	NPD7146	Approved
0.6742	Remote Similarity	NPD7521	Approved
0.6742	Remote Similarity	NPD6409	Approved
0.6742	Remote Similarity	NPD5786	Approved
0.6742	Remote Similarity	NPD6684	Approved
0.6742	Remote Similarity	NPD5330	Approved
0.6742	Remote Similarity	NPD7334	Approved
0.67	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6629	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD6903	Approved
0.6593	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4225	Approved
0.6489	Remote Similarity	NPD6399	Phase 3
0.6437	Remote Similarity	NPD5368	Approved
0.6437	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5737	Approved
0.6413	Remote Similarity	NPD6672	Approved
0.6383	Remote Similarity	NPD5693	Phase 1
0.6279	Remote Similarity	NPD4756	Discovery
0.6277	Remote Similarity	NPD5207	Approved
0.6277	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7331	Phase 2
0.625	Remote Similarity	NPD4819	Approved
0.6222	Remote Similarity	NPD5332	Approved
0.6222	Remote Similarity	NPD5331	Approved
0.6211	Remote Similarity	NPD7983	Approved
0.6207	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD4271	Approved
0.6196	Remote Similarity	NPD6422	Discontinued
0.6196	Remote Similarity	NPD4249	Approved
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4790	Discontinued
0.617	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6101	Approved
0.617	Remote Similarity	NPD5370	Suspended
0.6162	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5779	Approved
0.6146	Remote Similarity	NPD5778	Approved
0.6132	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3573	Approved
0.6129	Remote Similarity	NPD4250	Approved
0.6129	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD6008	Approved
0.6111	Remote Similarity	NPD28	Approved
0.6111	Remote Similarity	NPD29	Approved
0.6111	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD6927	Phase 3
0.6082	Remote Similarity	NPD7748	Approved
0.6082	Remote Similarity	NPD6001	Approved
0.6081	Remote Similarity	NPD9298	Approved
0.6064	Remote Similarity	NPD5208	Approved
0.6061	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD6411	Approved
0.6042	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3618	Phase 1
0.6022	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3197	Phase 1
0.5981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3133	Approved
0.5978	Remote Similarity	NPD4786	Approved
0.5978	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3668	Phase 3
0.5978	Remote Similarity	NPD3666	Approved
0.5978	Remote Similarity	NPD3665	Phase 1
0.596	Remote Similarity	NPD7839	Suspended
0.596	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD3172	Approved
0.5941	Remote Similarity	NPD7639	Approved
0.5941	Remote Similarity	NPD7640	Approved
0.5938	Remote Similarity	NPD5692	Phase 3
0.5926	Remote Similarity	NPD7341	Phase 2
0.5926	Remote Similarity	NPD6053	Discontinued
0.59	Remote Similarity	NPD6084	Phase 2
0.59	Remote Similarity	NPD6083	Phase 2
0.5889	Remote Similarity	NPD4695	Discontinued
0.5888	Remote Similarity	NPD2067	Discontinued
0.5876	Remote Similarity	NPD5694	Approved
0.5876	Remote Similarity	NPD6050	Approved
0.5876	Remote Similarity	NPD7515	Phase 2
0.5875	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD3194	Approved
0.5867	Remote Similarity	NPD3195	Phase 2
0.5867	Remote Similarity	NPD4266	Approved
0.5867	Remote Similarity	NPD3196	Approved
0.5851	Remote Similarity	NPD5279	Phase 3
0.5833	Remote Similarity	NPD6051	Approved
0.5765	Remote Similarity	NPD4691	Approved
0.5755	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD5281	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD5284	Approved
0.5714	Remote Similarity	NPD6079	Approved
0.5701	Remote Similarity	NPD6881	Approved
0.5701	Remote Similarity	NPD6899	Approved
0.5701	Remote Similarity	NPD6011	Approved
0.5694	Remote Similarity	NPD5343	Approved
0.5688	Remote Similarity	NPD6650	Approved
0.5688	Remote Similarity	NPD6649	Approved
0.567	Remote Similarity	NPD5328	Approved
0.5663	Remote Similarity	NPD3704	Approved
0.566	Remote Similarity	NPD7128	Approved
0.566	Remote Similarity	NPD6402	Approved
0.566	Remote Similarity	NPD5739	Approved
0.566	Remote Similarity	NPD6675	Approved
0.5652	Remote Similarity	NPD857	Phase 3
0.5648	Remote Similarity	NPD6014	Approved
0.5648	Remote Similarity	NPD6372	Approved
0.5648	Remote Similarity	NPD6012	Approved
0.5648	Remote Similarity	NPD6373	Approved
0.5648	Remote Similarity	NPD6013	Approved
0.5647	Remote Similarity	NPD4137	Phase 3
0.5634	Remote Similarity	NPD3174	Discontinued
0.5631	Remote Similarity	NPD6648	Approved
0.5625	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1145	Discontinued
0.5619	Remote Similarity	NPD6052	Approved
0.5619	Remote Similarity	NPD6647	Phase 2
0.5612	Remote Similarity	NPD3673	Approved
0.5612	Remote Similarity	NPD3672	Approved
0.5607	Remote Similarity	NPD5701	Approved
0.5607	Remote Similarity	NPD5954	Clinical (unspecified phase)

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