NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.804
LogD:	1.979
LogS:	-2.461
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	4.312
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:	-4.665
MDCK Permeability:	4.1326406062580645e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	86.34127044677734%
Volume Distribution (VD):	1.34
Pgp-substrate:	12.753759384155273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.306
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.171
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.554
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.275
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	10.007
Half-life (T1/2):	0.536

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.197
Carcinogencity:	0.933
Eye Corrosion:	0.036
Eye Irritation:	0.737
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC470244

Natural Product ID:	NPC470244
*Common Name:**	4H-Tomentosin
IUPAC Name:	(3aR,7S,8aR)-6-(3-hydroxybutyl)-7-methyl-3-methylidene-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
Synonyms:	4H-Tomentosin
Standard InCHIKey:	KQEADOUDJYBGFC-AIHGEPKZSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9-10,13-14,16H,3-5,7-8H2,1-2H3/t9-,10?,13+,14+/m0/s1
SMILES:	CC(CCC1=CC[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1912056
PubChem CID:	15109105
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
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
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
IC50	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5480.0	nM	PMID[506811]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	>	128.0	ug.mL-1	PMID[506812]

☑ 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 NPC470244 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	160
0.1-0.2	1032
0.2-0.3	5144
0.3-0.4	14448
0.4-0.5	10571
0.5-0.6	6707
0.6-0.7	3577
0.7-0.8	878
0.8-0.85	108
0.85-0.9	59
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470239
0.9241	High Similarity	NPC165162
0.92	High Similarity	NPC476794
0.92	High Similarity	NPC65603
0.92	High Similarity	NPC470240
0.9189	High Similarity	NPC226669
0.9189	High Similarity	NPC138408
0.9189	High Similarity	NPC193351
0.9103	High Similarity	NPC89555
0.9054	High Similarity	NPC472966
0.8961	High Similarity	NPC182550
0.8947	High Similarity	NPC320630
0.8947	High Similarity	NPC116177
0.8947	High Similarity	NPC7563
0.8875	High Similarity	NPC191476
0.8875	High Similarity	NPC156485
0.8875	High Similarity	NPC114979
0.8846	High Similarity	NPC302426
0.8831	High Similarity	NPC471465
0.8831	High Similarity	NPC196653
0.8816	High Similarity	NPC235906
0.8795	High Similarity	NPC268298
0.8765	High Similarity	NPC255307
0.8734	High Similarity	NPC301477
0.8734	High Similarity	NPC281949
0.8734	High Similarity	NPC25684
0.8718	High Similarity	NPC63649
0.8718	High Similarity	NPC167881
0.8718	High Similarity	NPC89128
0.8718	High Similarity	NPC264227
0.8718	High Similarity	NPC98557
0.8718	High Similarity	NPC472965
0.869	High Similarity	NPC129419
0.8684	High Similarity	NPC155587
0.8659	High Similarity	NPC150755
0.8659	High Similarity	NPC67493
0.8659	High Similarity	NPC475461
0.8659	High Similarity	NPC305475
0.8642	High Similarity	NPC96259
0.8642	High Similarity	NPC141193
0.8625	High Similarity	NPC229825
0.8608	High Similarity	NPC276356
0.859	High Similarity	NPC472960
0.859	High Similarity	NPC108816
0.859	High Similarity	NPC267231
0.859	High Similarity	NPC93763
0.8533	High Similarity	NPC163003
0.8519	High Similarity	NPC131669
0.8519	High Similarity	NPC250315
0.8519	High Similarity	NPC473390
0.85	High Similarity	NPC470241
0.85	High Similarity	NPC10276
0.85	High Similarity	NPC24417
0.85	High Similarity	NPC35089
0.8481	Intermediate Similarity	NPC617
0.8471	Intermediate Similarity	NPC301969
0.8471	Intermediate Similarity	NPC37607
0.8462	Intermediate Similarity	NPC187568
0.8462	Intermediate Similarity	NPC41780
0.8452	Intermediate Similarity	NPC91248
0.8452	Intermediate Similarity	NPC202672
0.8421	Intermediate Similarity	NPC58956
0.8421	Intermediate Similarity	NPC295633
0.8421	Intermediate Similarity	NPC269206
0.8415	Intermediate Similarity	NPC165287
0.8415	Intermediate Similarity	NPC476804
0.8415	Intermediate Similarity	NPC115786
0.84	Intermediate Similarity	NPC472955
0.8395	Intermediate Similarity	NPC474291
0.8375	Intermediate Similarity	NPC69271
0.8375	Intermediate Similarity	NPC74673
0.8372	Intermediate Similarity	NPC131209
0.8353	Intermediate Similarity	NPC295312
0.8333	Intermediate Similarity	NPC237540
0.8312	Intermediate Similarity	NPC476355
0.8312	Intermediate Similarity	NPC140287
0.8295	Intermediate Similarity	NPC52044
0.8293	Intermediate Similarity	NPC40746
0.8293	Intermediate Similarity	NPC215294
0.8293	Intermediate Similarity	NPC39588
0.8293	Intermediate Similarity	NPC59097
0.8293	Intermediate Similarity	NPC318468
0.8293	Intermediate Similarity	NPC169575
0.8272	Intermediate Similarity	NPC52861
0.8272	Intermediate Similarity	NPC325031
0.8272	Intermediate Similarity	NPC141810
0.8267	Intermediate Similarity	NPC296522
0.8267	Intermediate Similarity	NPC144511
0.8256	Intermediate Similarity	NPC158488
0.8256	Intermediate Similarity	NPC469368
0.8235	Intermediate Similarity	NPC277771
0.8235	Intermediate Similarity	NPC477302
0.8235	Intermediate Similarity	NPC136879
0.8228	Intermediate Similarity	NPC15975
0.8228	Intermediate Similarity	NPC195785
0.8214	Intermediate Similarity	NPC261721
0.8214	Intermediate Similarity	NPC107787
0.8193	Intermediate Similarity	NPC472957
0.8193	Intermediate Similarity	NPC158756
0.8193	Intermediate Similarity	NPC472958
0.8193	Intermediate Similarity	NPC82297
0.8182	Intermediate Similarity	NPC472956
0.8171	Intermediate Similarity	NPC178676
0.8161	Intermediate Similarity	NPC208886
0.8161	Intermediate Similarity	NPC184463
0.8161	Intermediate Similarity	NPC30515
0.8161	Intermediate Similarity	NPC233345
0.8161	Intermediate Similarity	NPC133698
0.8161	Intermediate Similarity	NPC12172
0.8161	Intermediate Similarity	NPC186363
0.814	Intermediate Similarity	NPC206001
0.814	Intermediate Similarity	NPC307411
0.814	Intermediate Similarity	NPC218927
0.814	Intermediate Similarity	NPC474032
0.8125	Intermediate Similarity	NPC299235
0.8118	Intermediate Similarity	NPC160138
0.8111	Intermediate Similarity	NPC161493
0.8101	Intermediate Similarity	NPC123360
0.8101	Intermediate Similarity	NPC472967
0.8101	Intermediate Similarity	NPC472959
0.8101	Intermediate Similarity	NPC266159
0.8095	Intermediate Similarity	NPC21469
0.8095	Intermediate Similarity	NPC78089
0.8095	Intermediate Similarity	NPC470755
0.8095	Intermediate Similarity	NPC161957
0.8095	Intermediate Similarity	NPC21471
0.8095	Intermediate Similarity	NPC33570
0.8095	Intermediate Similarity	NPC235792
0.809	Intermediate Similarity	NPC170120
0.809	Intermediate Similarity	NPC193645
0.809	Intermediate Similarity	NPC48803
0.809	Intermediate Similarity	NPC304886
0.809	Intermediate Similarity	NPC213698
0.809	Intermediate Similarity	NPC90121
0.809	Intermediate Similarity	NPC275960
0.809	Intermediate Similarity	NPC67584
0.8077	Intermediate Similarity	NPC143979
0.8077	Intermediate Similarity	NPC320537
0.8072	Intermediate Similarity	NPC272814
0.8072	Intermediate Similarity	NPC245665
0.8068	Intermediate Similarity	NPC212486
0.8068	Intermediate Similarity	NPC475838
0.8068	Intermediate Similarity	NPC469645
0.8068	Intermediate Similarity	NPC81419
0.8068	Intermediate Similarity	NPC228451
0.8068	Intermediate Similarity	NPC469692
0.8068	Intermediate Similarity	NPC475302
0.8068	Intermediate Similarity	NPC125674
0.8068	Intermediate Similarity	NPC475912
0.8068	Intermediate Similarity	NPC179746
0.8052	Intermediate Similarity	NPC129665
0.8046	Intermediate Similarity	NPC476004
0.8046	Intermediate Similarity	NPC475855
0.8046	Intermediate Similarity	NPC474761
0.8046	Intermediate Similarity	NPC51004
0.8025	Intermediate Similarity	NPC19841
0.8023	Intermediate Similarity	NPC476805
0.8023	Intermediate Similarity	NPC476803
0.8	Intermediate Similarity	NPC171204
0.8	Intermediate Similarity	NPC284902
0.8	Intermediate Similarity	NPC469910
0.8	Intermediate Similarity	NPC213078
0.8	Intermediate Similarity	NPC470242
0.8	Intermediate Similarity	NPC141789
0.8	Intermediate Similarity	NPC476028
0.8	Intermediate Similarity	NPC236692
0.8	Intermediate Similarity	NPC97516
0.8	Intermediate Similarity	NPC309757
0.8	Intermediate Similarity	NPC56593
0.7978	Intermediate Similarity	NPC167219
0.7978	Intermediate Similarity	NPC323008
0.7978	Intermediate Similarity	NPC474035
0.7978	Intermediate Similarity	NPC477131
0.7978	Intermediate Similarity	NPC81386
0.7978	Intermediate Similarity	NPC474247
0.7978	Intermediate Similarity	NPC470010
0.7978	Intermediate Similarity	NPC121825
0.7978	Intermediate Similarity	NPC262133
0.7978	Intermediate Similarity	NPC127019
0.7978	Intermediate Similarity	NPC470013
0.7978	Intermediate Similarity	NPC198853
0.7976	Intermediate Similarity	NPC224386
0.7976	Intermediate Similarity	NPC194859
0.7976	Intermediate Similarity	NPC9868
0.7955	Intermediate Similarity	NPC261607
0.7955	Intermediate Similarity	NPC111114
0.7955	Intermediate Similarity	NPC300312
0.7952	Intermediate Similarity	NPC173609
0.7931	Intermediate Similarity	NPC168131
0.7927	Intermediate Similarity	NPC223904
0.7927	Intermediate Similarity	NPC233377
0.7912	Intermediate Similarity	NPC169205
0.7907	Intermediate Similarity	NPC312561
0.7907	Intermediate Similarity	NPC248602
0.7901	Intermediate Similarity	NPC128276
0.7889	Intermediate Similarity	NPC14961
0.7889	Intermediate Similarity	NPC36954
0.7889	Intermediate Similarity	NPC270013
0.7889	Intermediate Similarity	NPC183012
0.7882	Intermediate Similarity	NPC300082

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 NPC470244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1587
0.2-0.3	3855
0.3-0.4	2421
0.4-0.5	701
0.5-0.6	344
0.6-0.7	74
0.7-0.8	18
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
0.809	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1695	Approved
0.7674	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1694	Approved
0.7444	Intermediate Similarity	NPD5785	Approved
0.7442	Intermediate Similarity	NPD7154	Phase 3
0.7273	Intermediate Similarity	NPD5363	Approved
0.7253	Intermediate Similarity	NPD46	Approved
0.7253	Intermediate Similarity	NPD6698	Approved
0.7241	Intermediate Similarity	NPD5362	Discontinued
0.7209	Intermediate Similarity	NPD5369	Approved
0.7126	Intermediate Similarity	NPD4269	Approved
0.7126	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4270	Approved
0.71	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4225	Approved
0.7079	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD5786	Approved
0.6932	Remote Similarity	NPD6435	Approved
0.6897	Remote Similarity	NPD4252	Approved
0.6897	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7838	Discovery
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6101	Approved
0.6737	Remote Similarity	NPD6399	Phase 3
0.6737	Remote Similarity	NPD5778	Approved
0.6737	Remote Similarity	NPD5779	Approved
0.6706	Remote Similarity	NPD8039	Approved
0.6705	Remote Similarity	NPD4820	Approved
0.6705	Remote Similarity	NPD4821	Approved
0.6705	Remote Similarity	NPD5368	Approved
0.6705	Remote Similarity	NPD4822	Approved
0.6705	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6632	Remote Similarity	NPD7983	Approved
0.6632	Remote Similarity	NPD6411	Approved
0.663	Remote Similarity	NPD4249	Approved
0.6629	Remote Similarity	NPD4790	Discontinued
0.6566	Remote Similarity	NPD7638	Approved
0.6566	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4250	Approved
0.6559	Remote Similarity	NPD4251	Approved
0.6556	Remote Similarity	NPD5209	Approved
0.6556	Remote Similarity	NPD3667	Approved
0.6538	Remote Similarity	NPD6686	Approved
0.6509	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3197	Phase 1
0.65	Remote Similarity	NPD7640	Approved
0.65	Remote Similarity	NPD7639	Approved
0.6495	Remote Similarity	NPD5282	Discontinued
0.6452	Remote Similarity	NPD7521	Approved
0.6452	Remote Similarity	NPD7334	Approved
0.6452	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD5330	Approved
0.6452	Remote Similarity	NPD6684	Approved
0.6452	Remote Similarity	NPD7146	Approved
0.6449	Remote Similarity	NPD6053	Discontinued
0.6421	Remote Similarity	NPD5370	Suspended
0.6413	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3133	Approved
0.6413	Remote Similarity	NPD4786	Approved
0.6413	Remote Similarity	NPD3666	Approved
0.6413	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD7839	Suspended
0.6364	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD7115	Discovery
0.6341	Remote Similarity	NPD7331	Phase 2
0.6327	Remote Similarity	NPD7748	Approved
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7902	Approved
0.63	Remote Similarity	NPD6083	Phase 2
0.63	Remote Similarity	NPD6084	Phase 2
0.6289	Remote Similarity	NPD7515	Phase 2
0.6289	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD6422	Discontinued
0.6267	Remote Similarity	NPD3172	Approved
0.6263	Remote Similarity	NPD5695	Phase 3
0.6238	Remote Similarity	NPD5696	Approved
0.622	Remote Similarity	NPD7341	Phase 2
0.6184	Remote Similarity	NPD3194	Approved
0.6184	Remote Similarity	NPD3195	Phase 2
0.6184	Remote Similarity	NPD3196	Approved
0.6184	Remote Similarity	NPD4266	Approved
0.6154	Remote Similarity	NPD4695	Discontinued
0.6146	Remote Similarity	NPD5737	Approved
0.6146	Remote Similarity	NPD6672	Approved
0.6132	Remote Similarity	NPD5697	Approved
0.6125	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6079	Approved
0.6122	Remote Similarity	NPD5693	Phase 1
0.6122	Remote Similarity	NPD7637	Suspended
0.6117	Remote Similarity	NPD5344	Discontinued
0.6087	Remote Similarity	NPD857	Phase 3
0.6082	Remote Similarity	NPD5328	Approved
0.6075	Remote Similarity	NPD6011	Approved
0.6075	Remote Similarity	NPD6899	Approved
0.6075	Remote Similarity	NPD6881	Approved
0.6055	Remote Similarity	NPD6649	Approved
0.6055	Remote Similarity	NPD6650	Approved
0.6038	Remote Similarity	NPD6402	Approved
0.6038	Remote Similarity	NPD7128	Approved
0.6038	Remote Similarity	NPD5739	Approved
0.6038	Remote Similarity	NPD6675	Approved
0.602	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD6372	Approved
0.6019	Remote Similarity	NPD6014	Approved
0.6019	Remote Similarity	NPD6012	Approved
0.6019	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3198	Approved
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5701	Approved
0.5976	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7102	Approved
0.5963	Remote Similarity	NPD7290	Approved
0.5963	Remote Similarity	NPD6883	Approved
0.596	Remote Similarity	NPD5284	Approved
0.596	Remote Similarity	NPD8034	Phase 2
0.596	Remote Similarity	NPD5281	Approved
0.596	Remote Similarity	NPD8035	Phase 2
0.5952	Remote Similarity	NPD3704	Approved
0.5941	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5210	Approved
0.5941	Remote Similarity	NPD4629	Approved
0.5934	Remote Similarity	NPD3732	Approved
0.5926	Remote Similarity	NPD7320	Approved
0.5918	Remote Similarity	NPD4753	Phase 2
0.5909	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8130	Phase 1
0.5909	Remote Similarity	NPD6617	Approved
0.5909	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD6869	Approved
0.5905	Remote Similarity	NPD7632	Discontinued
0.59	Remote Similarity	NPD4202	Approved
0.59	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD342	Phase 1
0.5895	Remote Similarity	NPD3668	Phase 3
0.5888	Remote Similarity	NPD6008	Approved
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD5221	Approved
0.5882	Remote Similarity	NPD5222	Approved
0.5882	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3573	Approved
0.5872	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6648	Approved
0.5862	Remote Similarity	NPD8515	Approved
0.5862	Remote Similarity	NPD8517	Approved
0.5862	Remote Similarity	NPD8516	Approved
0.5862	Remote Similarity	NPD8513	Phase 3
0.5856	Remote Similarity	NPD6882	Approved
0.5856	Remote Similarity	NPD8297	Approved
0.5854	Remote Similarity	NPD368	Approved
0.5851	Remote Similarity	NPD4223	Phase 3
0.5851	Remote Similarity	NPD4221	Approved
0.5849	Remote Similarity	NPD6647	Phase 2
0.5843	Remote Similarity	NPD6924	Approved
0.5843	Remote Similarity	NPD6926	Approved
0.5842	Remote Similarity	NPD6001	Approved
0.5833	Remote Similarity	NPD1696	Phase 3
0.5825	Remote Similarity	NPD5173	Approved
0.5818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5208	Approved
0.5811	Remote Similarity	NPD622	Approved
0.5806	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6927	Phase 3
0.5789	Remote Similarity	NPD4788	Approved
0.5789	Remote Similarity	NPD28	Approved
0.5789	Remote Similarity	NPD29	Approved
0.5789	Remote Similarity	NPD6695	Phase 3
0.5773	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4519	Discontinued
0.5773	Remote Similarity	NPD6098	Approved
0.5773	Remote Similarity	NPD4623	Approved
0.5773	Remote Similarity	NPD5690	Phase 2
0.5769	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6673	Approved
0.5758	Remote Similarity	NPD6904	Approved
0.5758	Remote Similarity	NPD6080	Approved
0.5758	Remote Similarity	NPD6051	Approved
0.5758	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5211	Phase 2
0.5753	Remote Similarity	NPD634	Phase 3
0.5733	Remote Similarity	NPD3173	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