NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.08
Volume:	217.741
LogP:	0.546
LogD:	0.977
LogS:	-0.788
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	4.164
Fsp3:	0.545
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:	-4.736
MDCK Permeability:	0.00012300099479034543
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.145
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.875
Plasma Protein Binding (PPB):	35.786155700683594%
Volume Distribution (VD):	1.033
Pgp-substrate:	69.15340423583984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	6.339
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.51
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.947
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.828
Skin Sensitization:	0.435
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.176
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC188717

Natural Product ID:	NPC188717
*Common Name:**	Methyl (1R)-1-Hydroxy-7-(Hydroxymethyl)-1,4A,5,7A-Tetrahydrocyclopenta[C]Pyran-4-Carboxylate
IUPAC Name:	methyl (1R)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:
Standard InCHIKey:	AZKVWQKMDGGDSV-LKXRVVKTSA-N
Standard InCHI:	InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7?,9?,11-/m1/s1
SMILES:	COC(=O)C1=CO[C@H](C2C(=CCC12)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1317787
PubChem CID:	44144320
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO17824	Genipa americana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425120]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO17824	Genipa americana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1667413]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO17824	Genipa americana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8095	Fructus gardeniae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8095	Fructus gardeniae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17824	Genipa americana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17824	Genipa americana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	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
Potency	10

Activity Type	# Activity
Individual Protein	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[537654]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[537654]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	2059.6	nM	PMID[537654]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[537654]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[537654]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[537654]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[537654]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[537654]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[537654]

☑ 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 NPC188717 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	170
0.1-0.2	1320
0.2-0.3	5867
0.3-0.4	14436
0.4-0.5	13372
0.5-0.6	5873
0.6-0.7	1578
0.7-0.8	71
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC211455
0.9506	High Similarity	NPC142583
0.837	Intermediate Similarity	NPC255677
0.837	Intermediate Similarity	NPC22149
0.837	Intermediate Similarity	NPC306344
0.828	Intermediate Similarity	NPC28304
0.828	Intermediate Similarity	NPC298255
0.8105	Intermediate Similarity	NPC234304
0.8105	Intermediate Similarity	NPC267869
0.8105	Intermediate Similarity	NPC284929
0.8105	Intermediate Similarity	NPC197541
0.8105	Intermediate Similarity	NPC118761
0.8043	Intermediate Similarity	NPC241911
0.8021	Intermediate Similarity	NPC86095
0.8	Intermediate Similarity	NPC250545
0.8	Intermediate Similarity	NPC222062
0.8	Intermediate Similarity	NPC261117
0.8	Intermediate Similarity	NPC310804
0.7812	Intermediate Similarity	NPC195510
0.7812	Intermediate Similarity	NPC13171
0.7614	Intermediate Similarity	NPC212363
0.7527	Intermediate Similarity	NPC61201
0.7447	Intermediate Similarity	NPC475927
0.7447	Intermediate Similarity	NPC475832
0.7391	Intermediate Similarity	NPC307092
0.7347	Intermediate Similarity	NPC20673
0.7327	Intermediate Similarity	NPC254538
0.7327	Intermediate Similarity	NPC474285
0.7312	Intermediate Similarity	NPC303451
0.7312	Intermediate Similarity	NPC6414
0.7283	Intermediate Similarity	NPC473658
0.7273	Intermediate Similarity	NPC471599
0.7245	Intermediate Similarity	NPC244878
0.7204	Intermediate Similarity	NPC51358
0.7172	Intermediate Similarity	NPC219038
0.7143	Intermediate Similarity	NPC151093
0.7128	Intermediate Similarity	NPC117596
0.7097	Intermediate Similarity	NPC26078
0.7097	Intermediate Similarity	NPC473715
0.7083	Intermediate Similarity	NPC470010
0.7083	Intermediate Similarity	NPC262133
0.7083	Intermediate Similarity	NPC323008
0.7083	Intermediate Similarity	NPC470013
0.7079	Intermediate Similarity	NPC24417
0.7059	Intermediate Similarity	NPC153095
0.7053	Intermediate Similarity	NPC472126
0.7053	Intermediate Similarity	NPC472125
0.7053	Intermediate Similarity	NPC472124
0.7053	Intermediate Similarity	NPC131209
0.7033	Intermediate Similarity	NPC476804
0.7021	Intermediate Similarity	NPC268298
0.7011	Intermediate Similarity	NPC7563
0.7011	Intermediate Similarity	NPC320630
0.7011	Intermediate Similarity	NPC116177
0.701	Intermediate Similarity	NPC170204
0.701	Intermediate Similarity	NPC469543
0.7	Intermediate Similarity	NPC98859
0.7	Intermediate Similarity	NPC229825
0.7	Intermediate Similarity	NPC4637
0.697	Remote Similarity	NPC473307
0.6957	Remote Similarity	NPC21469
0.6947	Remote Similarity	NPC270908
0.6947	Remote Similarity	NPC216826
0.6947	Remote Similarity	NPC129419
0.6947	Remote Similarity	NPC65665
0.6947	Remote Similarity	NPC307699
0.6947	Remote Similarity	NPC120021
0.6947	Remote Similarity	NPC231710
0.6947	Remote Similarity	NPC470573
0.6939	Remote Similarity	NPC470801
0.6939	Remote Similarity	NPC306041
0.6932	Remote Similarity	NPC108816
0.6932	Remote Similarity	NPC196653
0.6932	Remote Similarity	NPC471465
0.6932	Remote Similarity	NPC93763
0.6923	Remote Similarity	NPC473390
0.6923	Remote Similarity	NPC169575
0.6923	Remote Similarity	NPC131669
0.6923	Remote Similarity	NPC40746
0.6923	Remote Similarity	NPC52923
0.6915	Remote Similarity	NPC475819
0.6907	Remote Similarity	NPC198853
0.6907	Remote Similarity	NPC477131
0.6897	Remote Similarity	NPC68819
0.6889	Remote Similarity	NPC52861
0.6875	Remote Similarity	NPC477783
0.6875	Remote Similarity	NPC133698
0.6875	Remote Similarity	NPC473321
0.6869	Remote Similarity	NPC153559
0.6867	Remote Similarity	NPC287705
0.6863	Remote Similarity	NPC475928
0.686	Remote Similarity	NPC476590
0.686	Remote Similarity	NPC114727
0.6854	Remote Similarity	NPC321728
0.6854	Remote Similarity	NPC167881
0.6854	Remote Similarity	NPC98557
0.6854	Remote Similarity	NPC323472
0.6848	Remote Similarity	NPC191476
0.6848	Remote Similarity	NPC158756
0.6848	Remote Similarity	NPC220167
0.6848	Remote Similarity	NPC136699
0.6848	Remote Similarity	NPC114979
0.6848	Remote Similarity	NPC96259
0.6848	Remote Similarity	NPC141193
0.6842	Remote Similarity	NPC295312
0.6842	Remote Similarity	NPC474032
0.6842	Remote Similarity	NPC87306
0.6837	Remote Similarity	NPC241407
0.6837	Remote Similarity	NPC101051
0.6837	Remote Similarity	NPC52044
0.6837	Remote Similarity	NPC291709
0.6837	Remote Similarity	NPC304886
0.6824	Remote Similarity	NPC67076
0.6824	Remote Similarity	NPC319163
0.6818	Remote Similarity	NPC315394
0.6809	Remote Similarity	NPC237540
0.6809	Remote Similarity	NPC74139
0.6809	Remote Similarity	NPC475678
0.6804	Remote Similarity	NPC475912
0.6804	Remote Similarity	NPC135776
0.6804	Remote Similarity	NPC166346
0.6804	Remote Similarity	NPC476049
0.68	Remote Similarity	NPC124181
0.68	Remote Similarity	NPC472015
0.6796	Remote Similarity	NPC305157
0.6796	Remote Similarity	NPC307846
0.6796	Remote Similarity	NPC474917
0.6774	Remote Similarity	NPC471223
0.6774	Remote Similarity	NPC470755
0.6774	Remote Similarity	NPC137033
0.6774	Remote Similarity	NPC255307
0.6774	Remote Similarity	NPC165162
0.6774	Remote Similarity	NPC67081
0.6771	Remote Similarity	NPC476004
0.6771	Remote Similarity	NPC475855
0.6771	Remote Similarity	NPC77337
0.6771	Remote Similarity	NPC474761
0.6771	Remote Similarity	NPC477782
0.6771	Remote Similarity	NPC473455
0.6771	Remote Similarity	NPC71533
0.6771	Remote Similarity	NPC106510
0.6771	Remote Similarity	NPC474232
0.6771	Remote Similarity	NPC473619
0.6768	Remote Similarity	NPC161293
0.6765	Remote Similarity	NPC475320
0.6765	Remote Similarity	NPC35185
0.6765	Remote Similarity	NPC474730
0.6765	Remote Similarity	NPC106668
0.6765	Remote Similarity	NPC177013
0.6765	Remote Similarity	NPC4899
0.6765	Remote Similarity	NPC86077
0.6762	Remote Similarity	NPC475960
0.6747	Remote Similarity	NPC59442
0.6742	Remote Similarity	NPC267231
0.6742	Remote Similarity	NPC264391
0.6739	Remote Similarity	NPC59097
0.6739	Remote Similarity	NPC250315
0.6739	Remote Similarity	NPC116543
0.6737	Remote Similarity	NPC476805
0.6737	Remote Similarity	NPC476803
0.6737	Remote Similarity	NPC91248
0.6737	Remote Similarity	NPC473151
0.6737	Remote Similarity	NPC475739
0.6737	Remote Similarity	NPC202672
0.6735	Remote Similarity	NPC303942
0.6735	Remote Similarity	NPC57405
0.6735	Remote Similarity	NPC475572
0.6735	Remote Similarity	NPC474035
0.6735	Remote Similarity	NPC81386
0.6731	Remote Similarity	NPC243998
0.6731	Remote Similarity	NPC170432
0.6706	Remote Similarity	NPC202011
0.6706	Remote Similarity	NPC67183
0.6705	Remote Similarity	NPC61863
0.6703	Remote Similarity	NPC325031
0.6702	Remote Similarity	NPC305475
0.6702	Remote Similarity	NPC469910
0.6702	Remote Similarity	NPC475461
0.6702	Remote Similarity	NPC47220
0.6702	Remote Similarity	NPC186332
0.6701	Remote Similarity	NPC9447
0.6701	Remote Similarity	NPC30515
0.67	Remote Similarity	NPC161493
0.67	Remote Similarity	NPC472290
0.6699	Remote Similarity	NPC27687
0.6699	Remote Similarity	NPC37240
0.6667	Remote Similarity	NPC212598
0.6667	Remote Similarity	NPC272050
0.6667	Remote Similarity	NPC67584
0.6667	Remote Similarity	NPC219966
0.6667	Remote Similarity	NPC32676
0.6667	Remote Similarity	NPC55304
0.6667	Remote Similarity	NPC471142
0.6667	Remote Similarity	NPC197813
0.6667	Remote Similarity	NPC3488
0.6667	Remote Similarity	NPC251528
0.6667	Remote Similarity	NPC91408
0.6667	Remote Similarity	NPC36954
0.6667	Remote Similarity	NPC477922
0.6667	Remote Similarity	NPC266718

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 NPC188717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1933
0.2-0.3	3968
0.3-0.4	2293
0.4-0.5	679
0.5-0.6	110
0.6-0.7	27
0.7-0.8	1
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
0.6739	Remote Similarity	NPD5362	Discontinued
0.6739	Remote Similarity	NPD7154	Phase 3
0.6702	Remote Similarity	NPD4249	Approved
0.6632	Remote Similarity	NPD4251	Approved
0.6632	Remote Similarity	NPD4250	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD46	Approved
0.6429	Remote Similarity	NPD5785	Approved
0.6429	Remote Similarity	NPD6698	Approved
0.6413	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6110	Phase 1
0.6374	Remote Similarity	NPD4268	Approved
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4271	Approved
0.6337	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1695	Approved
0.6316	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5363	Approved
0.6237	Remote Similarity	NPD4821	Approved
0.6237	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD4822	Approved
0.6237	Remote Similarity	NPD4252	Approved
0.6237	Remote Similarity	NPD4820	Approved
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.6186	Remote Similarity	NPD5786	Approved
0.6182	Remote Similarity	NPD6371	Approved
0.617	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4269	Approved
0.6105	Remote Similarity	NPD4270	Approved
0.6095	Remote Similarity	NPD7640	Approved
0.6095	Remote Similarity	NPD7639	Approved
0.6087	Remote Similarity	NPD4756	Discovery
0.6055	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7983	Approved
0.604	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD7638	Approved
0.598	Remote Similarity	NPD5778	Approved
0.598	Remote Similarity	NPD5779	Approved
0.5977	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7838	Discovery
0.5938	Remote Similarity	NPD6435	Approved
0.5938	Remote Similarity	NPD5209	Approved
0.5932	Remote Similarity	NPD8513	Phase 3
0.5918	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5368	Approved
0.5849	Remote Similarity	NPD4225	Approved
0.5841	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5369	Approved
0.581	Remote Similarity	NPD7839	Suspended
0.5798	Remote Similarity	NPD8517	Approved
0.5798	Remote Similarity	NPD8516	Approved
0.5798	Remote Similarity	NPD7503	Approved
0.5798	Remote Similarity	NPD8515	Approved
0.5769	Remote Similarity	NPD5282	Discontinued
0.5741	Remote Similarity	NPD5344	Discontinued
0.5738	Remote Similarity	NPD7507	Approved
0.5726	Remote Similarity	NPD7115	Discovery
0.5673	Remote Similarity	NPD6399	Phase 3
0.56	Remote Similarity	NPD1696	Phase 3
0.56	Remote Similarity	NPD1694	Approved
0.56	Remote Similarity	NPD7319	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