NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	286.925
LogP:	1.324
LogD:	1.205
LogS:	-1.44
# Rotatable Bonds:	4
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	4.423
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.696
MDCK Permeability:	0.00011538479157024994
Pgp-inhibitor:	0.056
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	31.961652755737305%
Volume Distribution (VD):	0.925
Pgp-substrate:	62.16419982910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.551
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	6.754
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.745
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.671
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.083
Carcinogencity:	0.54
Eye Corrosion:	0.009
Eye Irritation:	0.057
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC89555

Natural Product ID:	NPC89555
*Common Name:**	6Beta-Acetoxysundiversifolide
IUPAC Name:	[(3S,3aR,4S,7S,8aR)-6-(2-hydroxyethyl)-3,7-dimethyl-2-oxo-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-4-yl] acetate
Synonyms:
Standard InCHIKey:	RYPWQIGVZVKJLS-OOUKEXCNSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-8-6-12-14(9(2)15(18)20-12)13(19-10(3)17)7-11(8)4-5-16/h7-9,12-14,16H,4-6H2,1-3H3/t8-,9-,12+,13-,14+/m0/s1
SMILES:	OCCC1=C[C@H](OC(=O)C)[C@H]2[C@@H](C[C@@H]1C)OC(=O)[C@H]2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426501
PubChem CID:	72708602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO32526	lineariifolia turcz	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24044895]

☑ 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	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	>	50000.0	nM	PMID[547814]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[547814]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[547814]

☑ 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 NPC89555 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	168
0.1-0.2	1027
0.2-0.3	4438
0.3-0.4	12428
0.4-0.5	11875
0.5-0.6	7208
0.6-0.7	4285
0.7-0.8	1067
0.8-0.85	145
0.85-0.9	47
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC165162
0.9359	High Similarity	NPC470241
0.9114	High Similarity	NPC52861
0.9103	High Similarity	NPC470244
0.9103	High Similarity	NPC470239
0.9012	High Similarity	NPC191476
0.9012	High Similarity	NPC114979
0.8947	High Similarity	NPC472966
0.8902	High Similarity	NPC255307
0.8875	High Similarity	NPC281949
0.8875	High Similarity	NPC25684
0.8875	High Similarity	NPC301477
0.8861	High Similarity	NPC89128
0.8824	High Similarity	NPC129419
0.8795	High Similarity	NPC305475
0.8795	High Similarity	NPC475461
0.878	High Similarity	NPC165287
0.878	High Similarity	NPC96259
0.878	High Similarity	NPC141193
0.878	High Similarity	NPC476804
0.8765	High Similarity	NPC229825
0.8706	High Similarity	NPC268298
0.869	High Similarity	NPC237540
0.8675	High Similarity	NPC78089
0.8659	High Similarity	NPC473390
0.8659	High Similarity	NPC131669
0.8642	High Similarity	NPC24417
0.8636	High Similarity	NPC52044
0.8625	High Similarity	NPC98557
0.8625	High Similarity	NPC167881
0.8608	High Similarity	NPC476794
0.8608	High Similarity	NPC65603
0.8608	High Similarity	NPC470240
0.8605	High Similarity	NPC469368
0.8571	High Similarity	NPC150755
0.8571	High Similarity	NPC107787
0.8554	High Similarity	NPC156485
0.8553	High Similarity	NPC472955
0.8506	High Similarity	NPC131209
0.8444	Intermediate Similarity	NPC161493
0.8434	Intermediate Similarity	NPC40746
0.8434	Intermediate Similarity	NPC169575
0.8434	Intermediate Similarity	NPC59097
0.8427	Intermediate Similarity	NPC67584
0.8427	Intermediate Similarity	NPC170120
0.8427	Intermediate Similarity	NPC213698
0.8427	Intermediate Similarity	NPC304886
0.8415	Intermediate Similarity	NPC141810
0.8395	Intermediate Similarity	NPC182550
0.8375	Intermediate Similarity	NPC116177
0.8375	Intermediate Similarity	NPC7563
0.8375	Intermediate Similarity	NPC320630
0.8372	Intermediate Similarity	NPC136879
0.8372	Intermediate Similarity	NPC476805
0.8372	Intermediate Similarity	NPC477302
0.8372	Intermediate Similarity	NPC476803
0.8354	Intermediate Similarity	NPC138408
0.8354	Intermediate Similarity	NPC193351
0.8354	Intermediate Similarity	NPC226669
0.8333	Intermediate Similarity	NPC213078
0.8333	Intermediate Similarity	NPC115786
0.8333	Intermediate Similarity	NPC82297
0.8333	Intermediate Similarity	NPC158756
0.8333	Intermediate Similarity	NPC295799
0.8315	Intermediate Similarity	NPC470013
0.8315	Intermediate Similarity	NPC470010
0.8315	Intermediate Similarity	NPC323008
0.8315	Intermediate Similarity	NPC477131
0.8315	Intermediate Similarity	NPC127019
0.8315	Intermediate Similarity	NPC262133
0.8295	Intermediate Similarity	NPC133698
0.8295	Intermediate Similarity	NPC475925
0.8276	Intermediate Similarity	NPC212664
0.8276	Intermediate Similarity	NPC473564
0.8276	Intermediate Similarity	NPC218927
0.8276	Intermediate Similarity	NPC206001
0.8272	Intermediate Similarity	NPC471465
0.8272	Intermediate Similarity	NPC108816
0.8272	Intermediate Similarity	NPC93763
0.8272	Intermediate Similarity	NPC196653
0.825	Intermediate Similarity	NPC235906
0.8235	Intermediate Similarity	NPC470755
0.8222	Intermediate Similarity	NPC48803
0.8222	Intermediate Similarity	NPC90121
0.8222	Intermediate Similarity	NPC193645
0.8222	Intermediate Similarity	NPC275960
0.8205	Intermediate Similarity	NPC129665
0.8202	Intermediate Similarity	NPC475838
0.8202	Intermediate Similarity	NPC475912
0.8202	Intermediate Similarity	NPC228451
0.8202	Intermediate Similarity	NPC475302
0.8202	Intermediate Similarity	NPC125674
0.8193	Intermediate Similarity	NPC39411
0.8193	Intermediate Similarity	NPC255580
0.8182	Intermediate Similarity	NPC37607
0.8182	Intermediate Similarity	NPC301969
0.8182	Intermediate Similarity	NPC144511
0.8182	Intermediate Similarity	NPC296522
0.8182	Intermediate Similarity	NPC475855
0.8172	Intermediate Similarity	NPC150923
0.8171	Intermediate Similarity	NPC617
0.8161	Intermediate Similarity	NPC202672
0.8152	Intermediate Similarity	NPC141191
0.8152	Intermediate Similarity	NPC221615
0.8148	Intermediate Similarity	NPC97516
0.8148	Intermediate Similarity	NPC476028
0.8148	Intermediate Similarity	NPC474760
0.8148	Intermediate Similarity	NPC171204
0.8148	Intermediate Similarity	NPC141789
0.814	Intermediate Similarity	NPC469910
0.814	Intermediate Similarity	NPC67493
0.814	Intermediate Similarity	NPC236692
0.814	Intermediate Similarity	NPC309757
0.8118	Intermediate Similarity	NPC472958
0.8118	Intermediate Similarity	NPC472957
0.8111	Intermediate Similarity	NPC474247
0.8111	Intermediate Similarity	NPC167219
0.8111	Intermediate Similarity	NPC198853
0.8095	Intermediate Similarity	NPC474252
0.809	Intermediate Similarity	NPC184463
0.809	Intermediate Similarity	NPC30515
0.809	Intermediate Similarity	NPC300312
0.809	Intermediate Similarity	NPC261607
0.809	Intermediate Similarity	NPC111114
0.8072	Intermediate Similarity	NPC51507
0.8072	Intermediate Similarity	NPC276356
0.8072	Intermediate Similarity	NPC302426
0.8068	Intermediate Similarity	NPC295312
0.8065	Intermediate Similarity	NPC70865
0.8049	Intermediate Similarity	NPC267231
0.8043	Intermediate Similarity	NPC169205
0.8025	Intermediate Similarity	NPC68819
0.8022	Intermediate Similarity	NPC270013
0.8022	Intermediate Similarity	NPC14961
0.8022	Intermediate Similarity	NPC36954
0.8	Intermediate Similarity	NPC128246
0.8	Intermediate Similarity	NPC140287
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC318468
0.8	Intermediate Similarity	NPC469645
0.8	Intermediate Similarity	NPC474703
0.8	Intermediate Similarity	NPC212486
0.8	Intermediate Similarity	NPC476300
0.8	Intermediate Similarity	NPC135776
0.8	Intermediate Similarity	NPC81419
0.8	Intermediate Similarity	NPC476355
0.8	Intermediate Similarity	NPC250315
0.8	Intermediate Similarity	NPC469692
0.7978	Intermediate Similarity	NPC179394
0.7978	Intermediate Similarity	NPC51004
0.7978	Intermediate Similarity	NPC144133
0.7978	Intermediate Similarity	NPC473448
0.7976	Intermediate Similarity	NPC471325
0.7976	Intermediate Similarity	NPC325031
0.7975	Intermediate Similarity	NPC163003
0.7955	Intermediate Similarity	NPC473715
0.7955	Intermediate Similarity	NPC207114
0.7955	Intermediate Similarity	NPC91248
0.7955	Intermediate Similarity	NPC475819
0.7955	Intermediate Similarity	NPC217983
0.7952	Intermediate Similarity	NPC270126
0.7952	Intermediate Similarity	NPC475210
0.7952	Intermediate Similarity	NPC264227
0.7952	Intermediate Similarity	NPC19841
0.7952	Intermediate Similarity	NPC178277
0.7952	Intermediate Similarity	NPC63649
0.7952	Intermediate Similarity	NPC472965
0.7949	Intermediate Similarity	NPC101622
0.7935	Intermediate Similarity	NPC18019
0.7935	Intermediate Similarity	NPC24956
0.7935	Intermediate Similarity	NPC185553
0.7935	Intermediate Similarity	NPC279621
0.7935	Intermediate Similarity	NPC476315
0.7935	Intermediate Similarity	NPC230800
0.7931	Intermediate Similarity	NPC250981
0.7931	Intermediate Similarity	NPC470242
0.7931	Intermediate Similarity	NPC50637
0.7931	Intermediate Similarity	NPC469483
0.7931	Intermediate Similarity	NPC116575
0.7931	Intermediate Similarity	NPC187661
0.7931	Intermediate Similarity	NPC261721
0.7927	Intermediate Similarity	NPC187568
0.7927	Intermediate Similarity	NPC41780
0.7927	Intermediate Similarity	NPC15975
0.7927	Intermediate Similarity	NPC195785
0.7912	Intermediate Similarity	NPC474035
0.7912	Intermediate Similarity	NPC57405
0.7912	Intermediate Similarity	NPC474338
0.7912	Intermediate Similarity	NPC96541
0.7912	Intermediate Similarity	NPC121825
0.7912	Intermediate Similarity	NPC303942
0.7912	Intermediate Similarity	NPC81386
0.7907	Intermediate Similarity	NPC159635
0.7907	Intermediate Similarity	NPC474776
0.7901	Intermediate Similarity	NPC155587
0.7895	Intermediate Similarity	NPC86077
0.7889	Intermediate Similarity	NPC12172
0.7889	Intermediate Similarity	NPC186363
0.7889	Intermediate Similarity	NPC233345
0.7889	Intermediate Similarity	NPC208886

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 NPC89555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1548
0.2-0.3	3664
0.3-0.4	2536
0.4-0.5	768
0.5-0.6	368
0.6-0.7	81
0.7-0.8	31
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
0.8222	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7154	Phase 3
0.7667	Intermediate Similarity	NPD1695	Approved
0.7647	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5362	Discontinued
0.7582	Intermediate Similarity	NPD46	Approved
0.7582	Intermediate Similarity	NPD6698	Approved
0.7471	Intermediate Similarity	NPD4270	Approved
0.7471	Intermediate Similarity	NPD6435	Approved
0.7471	Intermediate Similarity	NPD4269	Approved
0.7442	Intermediate Similarity	NPD4822	Approved
0.7442	Intermediate Similarity	NPD4819	Approved
0.7442	Intermediate Similarity	NPD4821	Approved
0.7442	Intermediate Similarity	NPD4820	Approved
0.7412	Intermediate Similarity	NPD4268	Approved
0.7412	Intermediate Similarity	NPD4271	Approved
0.74	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5785	Approved
0.7356	Intermediate Similarity	NPD5369	Approved
0.7353	Intermediate Similarity	NPD6371	Approved
0.7333	Intermediate Similarity	NPD5786	Approved
0.7333	Intermediate Similarity	NPD4249	Approved
0.7253	Intermediate Similarity	NPD4251	Approved
0.7253	Intermediate Similarity	NPD4250	Approved
0.7241	Intermediate Similarity	NPD5368	Approved
0.7241	Intermediate Similarity	NPD4252	Approved
0.7234	Intermediate Similarity	NPD5778	Approved
0.7234	Intermediate Similarity	NPD5779	Approved
0.7222	Intermediate Similarity	NPD5363	Approved
0.7222	Intermediate Similarity	NPD1694	Approved
0.7222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4225	Approved
0.7209	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7983	Approved
0.7097	Intermediate Similarity	NPD6101	Approved
0.7097	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.7021	Intermediate Similarity	NPD7838	Discovery
0.7	Intermediate Similarity	NPD5331	Approved
0.7	Intermediate Similarity	NPD5332	Approved
0.6966	Remote Similarity	NPD4790	Discontinued
0.6952	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD6053	Discontinued
0.6827	Remote Similarity	NPD6686	Approved
0.6804	Remote Similarity	NPD5282	Discontinued
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD8039	Approved
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6598	Remote Similarity	NPD7637	Suspended
0.6585	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5370	Suspended
0.6559	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5209	Approved
0.6522	Remote Similarity	NPD3667	Approved
0.6486	Remote Similarity	NPD7115	Discovery
0.6436	Remote Similarity	NPD7902	Approved
0.6436	Remote Similarity	NPD6084	Phase 2
0.6436	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5344	Discontinued
0.6404	Remote Similarity	NPD8516	Approved
0.6404	Remote Similarity	NPD8515	Approved
0.6404	Remote Similarity	NPD8513	Phase 3
0.6404	Remote Similarity	NPD8517	Approved
0.64	Remote Similarity	NPD5695	Phase 3
0.6383	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.63	Remote Similarity	NPD7748	Approved
0.6296	Remote Similarity	NPD6372	Approved
0.6296	Remote Similarity	NPD6373	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3197	Phase 1
0.6263	Remote Similarity	NPD7515	Phase 2
0.6263	Remote Similarity	NPD8035	Phase 2
0.6263	Remote Similarity	NPD8034	Phase 2
0.6262	Remote Similarity	NPD5701	Approved
0.6262	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD6422	Discontinued
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.622	Remote Similarity	NPD368	Approved
0.6211	Remote Similarity	NPD3666	Approved
0.6211	Remote Similarity	NPD3665	Phase 1
0.6211	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3133	Approved
0.6204	Remote Similarity	NPD7320	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6182	Remote Similarity	NPD6649	Approved
0.6182	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD4756	Discovery
0.6154	Remote Similarity	NPD6648	Approved
0.6147	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6139	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7900	Approved
0.6134	Remote Similarity	NPD8074	Phase 3
0.6122	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6903	Approved
0.6122	Remote Similarity	NPD6672	Approved
0.6122	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6695	Phase 3
0.61	Remote Similarity	NPD5693	Phase 1
0.61	Remote Similarity	NPD5281	Approved
0.61	Remote Similarity	NPD5284	Approved
0.6098	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6082	Remote Similarity	NPD5279	Phase 3
0.6064	Remote Similarity	NPD857	Phase 3
0.6061	Remote Similarity	NPD6051	Approved
0.6061	Remote Similarity	NPD4753	Phase 2
0.6055	Remote Similarity	NPD6011	Approved
0.6047	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3668	Phase 3
0.604	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7632	Discontinued
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD6869	Approved
0.6026	Remote Similarity	NPD3172	Approved
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6008	Approved
0.5982	Remote Similarity	NPD8297	Approved
0.5982	Remote Similarity	NPD6882	Approved
0.5979	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3198	Approved
0.5963	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6685	Approved
0.5963	Remote Similarity	NPD6412	Phase 2
0.5962	Remote Similarity	NPD4755	Approved
0.5957	Remote Similarity	NPD4695	Discontinued
0.5949	Remote Similarity	NPD3194	Approved
0.5949	Remote Similarity	NPD3196	Approved
0.5949	Remote Similarity	NPD4266	Approved
0.5949	Remote Similarity	NPD3195	Phase 2
0.5946	Remote Similarity	NPD6420	Discontinued
0.593	Remote Similarity	NPD7331	Phase 2
0.5922	Remote Similarity	NPD4629	Approved
0.5922	Remote Similarity	NPD5210	Approved
0.5922	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7507	Approved
0.5917	Remote Similarity	NPD8273	Phase 1
0.5914	Remote Similarity	NPD3732	Approved
0.5909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5328	Approved
0.5893	Remote Similarity	NPD2204	Approved
0.5893	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD4202	Approved
0.5876	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD342	Phase 1
0.5865	Remote Similarity	NPD4228	Discovery
0.5865	Remote Similarity	NPD4697	Phase 3
0.5865	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7524	Approved
0.5859	Remote Similarity	NPD7750	Discontinued
0.5856	Remote Similarity	NPD6413	Approved
0.5851	Remote Similarity	NPD6929	Approved
0.5849	Remote Similarity	NPD5286	Approved
0.5849	Remote Similarity	NPD4700	Approved
0.5849	Remote Similarity	NPD4696	Approved
0.5849	Remote Similarity	NPD5285	Approved
0.5842	Remote Similarity	NPD5207	Approved
0.5833	Remote Similarity	NPD6647	Phase 2
0.5833	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6274	Approved
0.5824	Remote Similarity	NPD6926	Approved
0.5824	Remote Similarity	NPD6924	Approved
0.5814	Remote Similarity	NPD7341	Phase 2
0.5814	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD2067	Discontinued
0.5804	Remote Similarity	NPD6421	Discontinued
0.5795	Remote Similarity	NPD229	Approved
0.5789	Remote Similarity	NPD8133	Approved
0.5789	Remote Similarity	NPD6930	Phase 2
0.5789	Remote Similarity	NPD6931	Approved
0.5785	Remote Similarity	NPD8451	Approved
0.5784	Remote Similarity	NPD6079	Approved
0.578	Remote Similarity	NPD5141	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