NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	275.498
LogP:	0.995
LogD:	1.286
LogS:	-1.622
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	4.38
Fsp3:	0.6
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:	-4.496
MDCK Permeability:	2.3890872398624197e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.344
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.578
Plasma Protein Binding (PPB):	57.613380432128906%
Volume Distribution (VD):	0.854
Pgp-substrate:	37.72030258178711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.251
CYP1A2-substrate:	0.313
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	10.354
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.217
Carcinogencity:	0.93
Eye Corrosion:	0.044
Eye Irritation:	0.162
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC165162

Natural Product ID:	NPC165162
*Common Name:**	6Beta-Hydroxytomentosin
IUPAC Name:	(3aS,4S,7S,8aR)-4-hydroxy-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
Synonyms:	6Beta-Hydroxytomentosin
Standard InCHIKey:	ZKFQTXFRYQAIAT-IOEYQFCTSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-6-13-14(10(3)15(18)19-13)12(17)7-11(8)5-4-9(2)16/h7-8,12-14,17H,3-6H2,1-2H3/t8-,12-,13+,14-/m0/s1
SMILES:	CC(=O)CCC1=C[C@H](O)[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163801
PubChem CID:	46849500
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
NPO33493	inula lineariifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515062]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	13100.0	nM	PMID[514734]

☑ 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 NPC165162 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	171
0.1-0.2	1076
0.2-0.3	4552
0.3-0.4	10580
0.4-0.5	13888
0.5-0.6	6922
0.6-0.7	4070
0.7-0.8	1177
0.8-0.85	162
0.85-0.9	66
0.9-0.95	31
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9405	High Similarity	NPC129419
0.9383	High Similarity	NPC141193
0.9383	High Similarity	NPC191476
0.9383	High Similarity	NPC114979
0.9383	High Similarity	NPC96259
0.9375	High Similarity	NPC89555
0.9286	High Similarity	NPC268298
0.9268	High Similarity	NPC255307
0.925	High Similarity	NPC281949
0.925	High Similarity	NPC25684
0.925	High Similarity	NPC301477
0.925	High Similarity	NPC470241
0.9241	High Similarity	NPC470239
0.9241	High Similarity	NPC470244
0.9157	High Similarity	NPC475461
0.9157	High Similarity	NPC305475
0.9136	High Similarity	NPC229825
0.9024	High Similarity	NPC131669
0.9024	High Similarity	NPC473390
0.9012	High Similarity	NPC24417
0.8987	High Similarity	NPC65603
0.8916	High Similarity	NPC476804
0.8824	High Similarity	NPC237540
0.8795	High Similarity	NPC40746
0.8795	High Similarity	NPC169575
0.878	High Similarity	NPC52861
0.8765	High Similarity	NPC98557
0.8765	High Similarity	NPC167881
0.875	High Similarity	NPC320630
0.875	High Similarity	NPC7563
0.875	High Similarity	NPC116177
0.875	High Similarity	NPC470240
0.875	High Similarity	NPC476794
0.8736	High Similarity	NPC469368
0.8734	High Similarity	NPC138408
0.8734	High Similarity	NPC193351
0.8734	High Similarity	NPC226669
0.8721	High Similarity	NPC136879
0.8706	High Similarity	NPC107787
0.8706	High Similarity	NPC150755
0.869	High Similarity	NPC115786
0.869	High Similarity	NPC158756
0.869	High Similarity	NPC165287
0.8642	High Similarity	NPC196653
0.8642	High Similarity	NPC471465
0.8642	High Similarity	NPC108816
0.8642	High Similarity	NPC93763
0.8621	High Similarity	NPC206001
0.8621	High Similarity	NPC218927
0.8588	High Similarity	NPC78089
0.8588	High Similarity	NPC470755
0.8571	High Similarity	NPC59097
0.8556	High Similarity	NPC304886
0.8556	High Similarity	NPC170120
0.8556	High Similarity	NPC52044
0.8554	High Similarity	NPC141810
0.8539	High Similarity	NPC475912
0.8539	High Similarity	NPC475302
0.8539	High Similarity	NPC125674
0.8539	High Similarity	NPC475838
0.8539	High Similarity	NPC469645
0.8539	High Similarity	NPC469692
0.8539	High Similarity	NPC228451
0.8537	High Similarity	NPC89128
0.8523	High Similarity	NPC144133
0.8523	High Similarity	NPC179394
0.8523	High Similarity	NPC475855
0.8506	High Similarity	NPC477302
0.8506	High Similarity	NPC476805
0.8506	High Similarity	NPC476803
0.8488	Intermediate Similarity	NPC469910
0.8478	Intermediate Similarity	NPC141191
0.8471	Intermediate Similarity	NPC156485
0.8444	Intermediate Similarity	NPC167219
0.8444	Intermediate Similarity	NPC474247
0.8444	Intermediate Similarity	NPC121825
0.8444	Intermediate Similarity	NPC323008
0.8444	Intermediate Similarity	NPC470010
0.8444	Intermediate Similarity	NPC470013
0.8444	Intermediate Similarity	NPC262133
0.8434	Intermediate Similarity	NPC302426
0.8427	Intermediate Similarity	NPC261607
0.8427	Intermediate Similarity	NPC300312
0.8427	Intermediate Similarity	NPC131209
0.8427	Intermediate Similarity	NPC111114
0.8415	Intermediate Similarity	NPC267231
0.8409	Intermediate Similarity	NPC295312
0.8395	Intermediate Similarity	NPC68819
0.8395	Intermediate Similarity	NPC235906
0.8375	Intermediate Similarity	NPC114727
0.8375	Intermediate Similarity	NPC476590
0.8375	Intermediate Similarity	NPC472966
0.837	Intermediate Similarity	NPC169205
0.837	Intermediate Similarity	NPC161493
0.8353	Intermediate Similarity	NPC250315
0.8353	Intermediate Similarity	NPC318468
0.8352	Intermediate Similarity	NPC36954
0.8352	Intermediate Similarity	NPC213698
0.8352	Intermediate Similarity	NPC48803
0.8352	Intermediate Similarity	NPC90121
0.8352	Intermediate Similarity	NPC14961
0.8352	Intermediate Similarity	NPC275960
0.8352	Intermediate Similarity	NPC67584
0.8352	Intermediate Similarity	NPC193645
0.8352	Intermediate Similarity	NPC270013
0.8333	Intermediate Similarity	NPC273579
0.8333	Intermediate Similarity	NPC162205
0.8333	Intermediate Similarity	NPC295204
0.8333	Intermediate Similarity	NPC288240
0.8313	Intermediate Similarity	NPC264227
0.8313	Intermediate Similarity	NPC182550
0.8313	Intermediate Similarity	NPC617
0.8313	Intermediate Similarity	NPC270126
0.8313	Intermediate Similarity	NPC63649
0.8313	Intermediate Similarity	NPC472965
0.8298	Intermediate Similarity	NPC150923
0.8295	Intermediate Similarity	NPC475819
0.8295	Intermediate Similarity	NPC202672
0.8295	Intermediate Similarity	NPC473715
0.8293	Intermediate Similarity	NPC476028
0.8293	Intermediate Similarity	NPC141789
0.8293	Intermediate Similarity	NPC171204
0.8293	Intermediate Similarity	NPC97516
0.828	Intermediate Similarity	NPC221615
0.8276	Intermediate Similarity	NPC261721
0.8276	Intermediate Similarity	NPC236692
0.8276	Intermediate Similarity	NPC309757
0.8272	Intermediate Similarity	NPC155587
0.8261	Intermediate Similarity	NPC279621
0.8261	Intermediate Similarity	NPC476315
0.8261	Intermediate Similarity	NPC185553
0.8261	Intermediate Similarity	NPC213078
0.8261	Intermediate Similarity	NPC230800
0.8256	Intermediate Similarity	NPC472958
0.8256	Intermediate Similarity	NPC472957
0.8242	Intermediate Similarity	NPC57405
0.8242	Intermediate Similarity	NPC477131
0.8242	Intermediate Similarity	NPC303942
0.8242	Intermediate Similarity	NPC81386
0.8242	Intermediate Similarity	NPC474035
0.8242	Intermediate Similarity	NPC474338
0.8242	Intermediate Similarity	NPC127019
0.8242	Intermediate Similarity	NPC198853
0.8229	Intermediate Similarity	NPC100487
0.8222	Intermediate Similarity	NPC184463
0.8222	Intermediate Similarity	NPC475925
0.8222	Intermediate Similarity	NPC30515
0.8222	Intermediate Similarity	NPC133698
0.8202	Intermediate Similarity	NPC474032
0.8202	Intermediate Similarity	NPC212664
0.8182	Intermediate Similarity	NPC160138
0.8161	Intermediate Similarity	NPC21469
0.8161	Intermediate Similarity	NPC261380
0.8148	Intermediate Similarity	NPC476355
0.8148	Intermediate Similarity	NPC140287
0.814	Intermediate Similarity	NPC474703
0.814	Intermediate Similarity	NPC116543
0.8132	Intermediate Similarity	NPC135776
0.8132	Intermediate Similarity	NPC179746
0.8132	Intermediate Similarity	NPC476300
0.8132	Intermediate Similarity	NPC81419
0.8132	Intermediate Similarity	NPC212486
0.8125	Intermediate Similarity	NPC163003
0.8118	Intermediate Similarity	NPC325031
0.8118	Intermediate Similarity	NPC10276
0.8118	Intermediate Similarity	NPC255580
0.8118	Intermediate Similarity	NPC471325
0.8118	Intermediate Similarity	NPC39411
0.8118	Intermediate Similarity	NPC35089
0.8111	Intermediate Similarity	NPC476004
0.8111	Intermediate Similarity	NPC71533
0.8111	Intermediate Similarity	NPC473448
0.8111	Intermediate Similarity	NPC474761
0.8111	Intermediate Similarity	NPC106510
0.8111	Intermediate Similarity	NPC37607
0.8111	Intermediate Similarity	NPC474232
0.8111	Intermediate Similarity	NPC301969
0.8111	Intermediate Similarity	NPC77337
0.8111	Intermediate Similarity	NPC51004
0.8105	Intermediate Similarity	NPC110443
0.8105	Intermediate Similarity	NPC46998
0.8105	Intermediate Similarity	NPC133907
0.8105	Intermediate Similarity	NPC185141
0.8105	Intermediate Similarity	NPC128733
0.8095	Intermediate Similarity	NPC178277
0.8095	Intermediate Similarity	NPC19841
0.809	Intermediate Similarity	NPC217983
0.809	Intermediate Similarity	NPC207114
0.8085	Intermediate Similarity	NPC187268
0.8072	Intermediate Similarity	NPC41780
0.8072	Intermediate Similarity	NPC187568
0.8068	Intermediate Similarity	NPC187661
0.8068	Intermediate Similarity	NPC469483
0.8068	Intermediate Similarity	NPC67493
0.8068	Intermediate Similarity	NPC50637
0.8046	Intermediate Similarity	NPC159635
0.8046	Intermediate Similarity	NPC295799
0.8046	Intermediate Similarity	NPC82297
0.8043	Intermediate Similarity	NPC469632
0.8025	Intermediate Similarity	NPC269206

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 NPC165162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1582
0.2-0.3	3669
0.3-0.4	2489
0.4-0.5	801
0.5-0.6	333
0.6-0.7	89
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7154	Phase 3
0.7717	Intermediate Similarity	NPD5785	Approved
0.7647	Intermediate Similarity	NPD6371	Approved
0.7609	Intermediate Similarity	NPD1695	Approved
0.7556	Intermediate Similarity	NPD5363	Approved
0.7527	Intermediate Similarity	NPD46	Approved
0.7527	Intermediate Similarity	NPD6698	Approved
0.7416	Intermediate Similarity	NPD4269	Approved
0.7416	Intermediate Similarity	NPD4270	Approved
0.7386	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD1694	Approved
0.7353	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD5362	Discontinued
0.7283	Intermediate Similarity	NPD5786	Approved
0.7222	Intermediate Similarity	NPD6435	Approved
0.7191	Intermediate Similarity	NPD4822	Approved
0.7191	Intermediate Similarity	NPD4252	Approved
0.7191	Intermediate Similarity	NPD4819	Approved
0.7191	Intermediate Similarity	NPD4821	Approved
0.7191	Intermediate Similarity	NPD4820	Approved
0.7174	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4268	Approved
0.7159	Intermediate Similarity	NPD4271	Approved
0.7158	Intermediate Similarity	NPD7838	Discovery
0.7111	Intermediate Similarity	NPD5369	Approved
0.7097	Intermediate Similarity	NPD4249	Approved
0.7083	Intermediate Similarity	NPD7983	Approved
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4251	Approved
0.7021	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD5779	Approved
0.701	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD5368	Approved
0.6916	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6399	Phase 3
0.6832	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6686	Approved
0.6774	Remote Similarity	NPD5331	Approved
0.6774	Remote Similarity	NPD5332	Approved
0.6768	Remote Similarity	NPD5282	Discontinued
0.6757	Remote Similarity	NPD7115	Discovery
0.6739	Remote Similarity	NPD4790	Discontinued
0.6702	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5370	Suspended
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6697	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6634	Remote Similarity	NPD7839	Suspended
0.6602	Remote Similarity	NPD7640	Approved
0.6602	Remote Similarity	NPD7639	Approved
0.6566	Remote Similarity	NPD6411	Approved
0.6566	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5344	Discontinued
0.6505	Remote Similarity	NPD7638	Approved
0.6444	Remote Similarity	NPD8039	Approved
0.6408	Remote Similarity	NPD6084	Phase 2
0.6408	Remote Similarity	NPD6083	Phase 2
0.6408	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD7637	Suspended
0.6389	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD5695	Phase 3
0.6346	Remote Similarity	NPD5696	Approved
0.633	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD3667	Approved
0.6306	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD6649	Approved
0.6296	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD6402	Approved
0.6296	Remote Similarity	NPD6675	Approved
0.6296	Remote Similarity	NPD5739	Approved
0.6286	Remote Similarity	NPD6648	Approved
0.6275	Remote Similarity	NPD7748	Approved
0.6273	Remote Similarity	NPD6012	Approved
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD6014	Approved
0.6273	Remote Similarity	NPD6013	Approved
0.6273	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD8516	Approved
0.6239	Remote Similarity	NPD8517	Approved
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD8515	Approved
0.6239	Remote Similarity	NPD8513	Phase 3
0.6238	Remote Similarity	NPD7515	Phase 2
0.6224	Remote Similarity	NPD3618	Phase 1
0.6224	Remote Similarity	NPD7334	Approved
0.6224	Remote Similarity	NPD6684	Approved
0.6224	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD7521	Approved
0.6224	Remote Similarity	NPD5330	Approved
0.6216	Remote Similarity	NPD7290	Approved
0.6216	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD7102	Approved
0.6186	Remote Similarity	NPD4786	Approved
0.6186	Remote Similarity	NPD3665	Phase 1
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD3133	Approved
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD7320	Approved
0.6168	Remote Similarity	NPD5211	Phase 2
0.6161	Remote Similarity	NPD6869	Approved
0.6161	Remote Similarity	NPD6617	Approved
0.6161	Remote Similarity	NPD6847	Approved
0.6161	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7900	Approved
0.6117	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6647	Phase 2
0.6106	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD6882	Approved
0.6105	Remote Similarity	NPD4695	Discontinued
0.61	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD6672	Approved
0.61	Remote Similarity	NPD6903	Approved
0.6092	Remote Similarity	NPD7331	Phase 2
0.6078	Remote Similarity	NPD5693	Phase 1
0.6078	Remote Similarity	NPD5284	Approved
0.6078	Remote Similarity	NPD5281	Approved
0.6071	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6422	Discontinued
0.6061	Remote Similarity	NPD5279	Phase 3
0.6058	Remote Similarity	NPD5210	Approved
0.6058	Remote Similarity	NPD4629	Approved
0.6055	Remote Similarity	NPD5141	Approved
0.6047	Remote Similarity	NPD3197	Phase 1
0.604	Remote Similarity	NPD4753	Phase 2
0.6023	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7632	Discontinued
0.6018	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD368	Approved
0.6	Remote Similarity	NPD6008	Approved
0.5984	Remote Similarity	NPD8074	Phase 3
0.5981	Remote Similarity	NPD5285	Approved
0.5981	Remote Similarity	NPD5286	Approved
0.5981	Remote Similarity	NPD4696	Approved
0.5977	Remote Similarity	NPD7341	Phase 2
0.596	Remote Similarity	NPD1696	Phase 3
0.5948	Remote Similarity	NPD6274	Approved
0.5946	Remote Similarity	NPD6412	Phase 2
0.5943	Remote Similarity	NPD4755	Approved
0.593	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD8034	Phase 2
0.5922	Remote Similarity	NPD6079	Approved
0.5922	Remote Similarity	NPD8035	Phase 2
0.5918	Remote Similarity	NPD6110	Phase 1
0.5918	Remote Similarity	NPD6695	Phase 3
0.5909	Remote Similarity	NPD3704	Approved
0.5905	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8273	Phase 1
0.59	Remote Similarity	NPD4519	Discontinued
0.59	Remote Similarity	NPD4623	Approved
0.5882	Remote Similarity	NPD5328	Approved
0.5877	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5225	Approved
0.5872	Remote Similarity	NPD4633	Approved
0.5872	Remote Similarity	NPD5226	Approved
0.5872	Remote Similarity	NPD5224	Approved
0.5868	Remote Similarity	NPD7642	Approved
0.5865	Remote Similarity	NPD4202	Approved
0.5859	Remote Similarity	NPD3668	Phase 3
0.5854	Remote Similarity	NPD342	Phase 1
0.5849	Remote Similarity	NPD5222	Approved
0.5849	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD4697	Phase 3
0.5849	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5221	Approved
0.5847	Remote Similarity	NPD7641	Discontinued
0.5841	Remote Similarity	NPD6413	Approved
0.5833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4700	Approved
0.5825	Remote Similarity	NPD5207	Approved
0.5818	Remote Similarity	NPD5174	Approved
0.5818	Remote Similarity	NPD5175	Approved
0.5816	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3172	Approved
0.5798	Remote Similarity	NPD7101	Approved
0.5798	Remote Similarity	NPD7100	Approved
0.5794	Remote Similarity	NPD7260	Phase 2
0.5794	Remote Similarity	NPD5173	Approved
0.5789	Remote Similarity	NPD6421	Discontinued
0.5789	Remote Similarity	NPD6420	Discontinued
0.5789	Remote Similarity	NPD2067	Discontinued
0.578	Remote Similarity	NPD5223	Approved
0.5776	Remote Similarity	NPD4632	Approved
0.5773	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7507	Approved
0.5763	Remote Similarity	NPD7505	Discontinued
0.5763	Remote Similarity	NPD7500	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