NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	442.34
Volume:	482.535
LogP:	6.269
LogD:	5.998
LogS:	-6.167
# Rotatable Bonds:	4
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	6.968
Fsp3:	0.931
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	6.829557241871953e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	91.9549789428711%
Volume Distribution (VD):	1.17
Pgp-substrate:	1.6691222190856934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	9.572
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.849
Human Hepatotoxicity (H-HT):	0.575
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.393
Carcinogencity:	0.01
Eye Corrosion:	0.859
Eye Irritation:	0.197
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC138942

Natural Product ID:	NPC138942
*Common Name:**	5,5'-Dipropylbiphenyl-2,2'-Diol
IUPAC Name:	2-(2-hydroxy-5-propylphenyl)-4-propylphenol
Synonyms:	tetrahydro-magnolol
Standard InCHIKey:	OYAQUBKYAKSHOA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H22O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h7-12,19-20H,3-6H2,1-2H3
SMILES:	CCCc1ccc(c(c1)c1cc(CCC)ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL32362
PubChem CID:	5321851
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls 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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17566	Magnolia biloba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17566	Magnolia biloba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17566	Magnolia biloba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17566	Magnolia biloba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	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
EC50	2
IC50	1
Ki	2
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	10
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2552	Individual Protein	Calcium-activated potassium channel subunit alpha-1	Homo sapiens	Control current	=	95.9	%	PMID[518151]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	23400.0	nM	PMID[518152]
NPT4120	Individual Protein	G-protein coupled receptor 55	Homo sapiens	Kb	=	13300.0	nM	PMID[518153]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ratio EC50	=	19.0	n.a.	PMID[518153]
NPT4120	Individual Protein	G-protein coupled receptor 55	Homo sapiens	Inhibition	=	96.0	%	PMID[518153]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Efficacy	=	49.0	%	PMID[518153]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Efficacy	=	124.0	%	PMID[518153]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	9010.0	nM	PMID[518153]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	416.0	nM	PMID[518153]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	2260.0	nM	PMID[518153]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	170.0	nM	PMID[518153]
NPT35	Others	n.a.		pKa	=	9.3	n.a.	PMID[518151]
NPT35	Others	n.a.		LogP	=	5.76	n.a.	PMID[518154]

☑ 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 NPC138942 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	259
0.1-0.2	1853
0.2-0.3	4494
0.3-0.4	13427
0.4-0.5	5787
0.5-0.6	8711
0.6-0.7	6164
0.7-0.8	1624
0.8-0.85	247
0.85-0.9	90
0.9-0.95	37
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC288411
0.9794	High Similarity	NPC168829
0.951	High Similarity	NPC296683
0.9505	High Similarity	NPC262365
0.9307	High Similarity	NPC271274
0.9307	High Similarity	NPC54765
0.9231	High Similarity	NPC95716
0.9231	High Similarity	NPC308689
0.9192	High Similarity	NPC225506
0.9184	High Similarity	NPC77492
0.9175	High Similarity	NPC26244
0.9151	High Similarity	NPC12656
0.9143	High Similarity	NPC286222
0.9143	High Similarity	NPC46940
0.9135	High Similarity	NPC44732
0.9126	High Similarity	NPC95344
0.9091	High Similarity	NPC92730
0.9091	High Similarity	NPC122005
0.9091	High Similarity	NPC252821
0.9082	High Similarity	NPC132271
0.9082	High Similarity	NPC473388
0.9082	High Similarity	NPC292730
0.9082	High Similarity	NPC82664
0.9082	High Similarity	NPC216520
0.9072	High Similarity	NPC128062
0.9072	High Similarity	NPC151715
0.9057	High Similarity	NPC35344
0.9057	High Similarity	NPC141003
0.9038	High Similarity	NPC58865
0.902	High Similarity	NPC99557
0.902	High Similarity	NPC219286
0.899	High Similarity	NPC225464
0.898	High Similarity	NPC8392
0.8972	High Similarity	NPC473137
0.8969	High Similarity	NPC271440
0.8962	High Similarity	NPC228988
0.8942	High Similarity	NPC63698
0.8942	High Similarity	NPC61885
0.8911	High Similarity	NPC51015
0.89	High Similarity	NPC128723
0.8879	High Similarity	NPC715
0.8868	High Similarity	NPC476632
0.8868	High Similarity	NPC4493
0.8868	High Similarity	NPC151537
0.8868	High Similarity	NPC165770
0.8868	High Similarity	NPC225679
0.8866	High Similarity	NPC204210
0.8866	High Similarity	NPC45040
0.8846	High Similarity	NPC151477
0.8824	High Similarity	NPC108497
0.8796	High Similarity	NPC195922
0.8796	High Similarity	NPC107240
0.8788	High Similarity	NPC274678
0.8788	High Similarity	NPC144682
0.8785	High Similarity	NPC43525
0.8785	High Similarity	NPC228425
0.8774	High Similarity	NPC13482
0.8762	High Similarity	NPC11554
0.8738	High Similarity	NPC238696
0.8727	High Similarity	NPC299180
0.8725	High Similarity	NPC12221
0.8713	High Similarity	NPC216468
0.8713	High Similarity	NPC132078
0.8713	High Similarity	NPC51333
0.8713	High Similarity	NPC78119
0.8704	High Similarity	NPC117846
0.8687	High Similarity	NPC289769
0.8687	High Similarity	NPC152415
0.8687	High Similarity	NPC76938
0.8687	High Similarity	NPC27323
0.8687	High Similarity	NPC316301
0.8679	High Similarity	NPC314187
0.8673	High Similarity	NPC304541
0.8667	High Similarity	NPC320439
0.8661	High Similarity	NPC475245
0.866	High Similarity	NPC70436
0.866	High Similarity	NPC177420
0.866	High Similarity	NPC242240
0.866	High Similarity	NPC318325
0.866	High Similarity	NPC123273
0.866	High Similarity	NPC280347
0.8654	High Similarity	NPC117115
0.8654	High Similarity	NPC474839
0.8641	High Similarity	NPC269212
0.8641	High Similarity	NPC233827
0.8627	High Similarity	NPC248396
0.8627	High Similarity	NPC48730
0.8627	High Similarity	NPC129373
0.8627	High Similarity	NPC213730
0.8614	High Similarity	NPC32674
0.8614	High Similarity	NPC152097
0.8614	High Similarity	NPC156313
0.8611	High Similarity	NPC250323
0.86	High Similarity	NPC32714
0.8598	High Similarity	NPC141782
0.8598	High Similarity	NPC132720
0.8571	High Similarity	NPC151197
0.8571	High Similarity	NPC55561
0.8571	High Similarity	NPC21594
0.8571	High Similarity	NPC248904
0.8571	High Similarity	NPC182240
0.8558	High Similarity	NPC323810
0.8558	High Similarity	NPC119860
0.8557	High Similarity	NPC25493
0.8557	High Similarity	NPC113460
0.8544	High Similarity	NPC40258
0.8544	High Similarity	NPC7686
0.8544	High Similarity	NPC91461
0.8532	High Similarity	NPC322239
0.8529	High Similarity	NPC260775
0.8519	High Similarity	NPC260323
0.8519	High Similarity	NPC266937
0.8519	High Similarity	NPC470770
0.8519	High Similarity	NPC77772
0.8519	High Similarity	NPC176279
0.8505	High Similarity	NPC254833
0.8505	High Similarity	NPC228343
0.8496	Intermediate Similarity	NPC473136
0.8491	Intermediate Similarity	NPC228737
0.8485	Intermediate Similarity	NPC155908
0.8485	Intermediate Similarity	NPC306074
0.8476	Intermediate Similarity	NPC233396
0.8476	Intermediate Similarity	NPC243677
0.8476	Intermediate Similarity	NPC47284
0.8476	Intermediate Similarity	NPC303141
0.8476	Intermediate Similarity	NPC154899
0.8469	Intermediate Similarity	NPC258219
0.8468	Intermediate Similarity	NPC261973
0.8468	Intermediate Similarity	NPC308828
0.8462	Intermediate Similarity	NPC168393
0.8455	Intermediate Similarity	NPC268160
0.8454	Intermediate Similarity	NPC307235
0.8454	Intermediate Similarity	NPC407
0.8454	Intermediate Similarity	NPC23167
0.8447	Intermediate Similarity	NPC294741
0.8447	Intermediate Similarity	NPC70677
0.8447	Intermediate Similarity	NPC72729
0.8447	Intermediate Similarity	NPC130756
0.8447	Intermediate Similarity	NPC211885
0.8447	Intermediate Similarity	NPC12931
0.844	Intermediate Similarity	NPC177962
0.844	Intermediate Similarity	NPC166995
0.844	Intermediate Similarity	NPC62867
0.8431	Intermediate Similarity	NPC475078
0.8431	Intermediate Similarity	NPC79241
0.8431	Intermediate Similarity	NPC6597
0.8421	Intermediate Similarity	NPC131868
0.8421	Intermediate Similarity	NPC129176
0.8416	Intermediate Similarity	NPC222146
0.8411	Intermediate Similarity	NPC201959
0.8411	Intermediate Similarity	NPC233835
0.8411	Intermediate Similarity	NPC470039
0.84	Intermediate Similarity	NPC3358
0.84	Intermediate Similarity	NPC306884
0.84	Intermediate Similarity	NPC147284
0.84	Intermediate Similarity	NPC94139
0.84	Intermediate Similarity	NPC162314
0.84	Intermediate Similarity	NPC210497
0.8396	Intermediate Similarity	NPC113457
0.8396	Intermediate Similarity	NPC67250
0.8396	Intermediate Similarity	NPC92623
0.8396	Intermediate Similarity	NPC155072
0.8396	Intermediate Similarity	NPC135464
0.8396	Intermediate Similarity	NPC53740
0.8396	Intermediate Similarity	NPC469913
0.8393	Intermediate Similarity	NPC470760
0.8393	Intermediate Similarity	NPC477136
0.8384	Intermediate Similarity	NPC192
0.8381	Intermediate Similarity	NPC8931
0.8381	Intermediate Similarity	NPC272029
0.8381	Intermediate Similarity	NPC327811
0.8381	Intermediate Similarity	NPC261573
0.8381	Intermediate Similarity	NPC475225
0.8381	Intermediate Similarity	NPC254965
0.8381	Intermediate Similarity	NPC120693
0.8378	Intermediate Similarity	NPC147179
0.8378	Intermediate Similarity	NPC192948
0.8378	Intermediate Similarity	NPC35797
0.8365	Intermediate Similarity	NPC252105
0.8365	Intermediate Similarity	NPC477685
0.8351	Intermediate Similarity	NPC155393
0.8351	Intermediate Similarity	NPC197783
0.835	Intermediate Similarity	NPC299762
0.835	Intermediate Similarity	NPC33675
0.8349	Intermediate Similarity	NPC224527
0.8348	Intermediate Similarity	NPC31936
0.8348	Intermediate Similarity	NPC251259
0.8333	Intermediate Similarity	NPC312132
0.8333	Intermediate Similarity	NPC259512
0.8333	Intermediate Similarity	NPC33728
0.8333	Intermediate Similarity	NPC202647
0.8333	Intermediate Similarity	NPC223451
0.8333	Intermediate Similarity	NPC19808
0.8319	Intermediate Similarity	NPC469609
0.8317	Intermediate Similarity	NPC245187
0.8304	Intermediate Similarity	NPC471668
0.8304	Intermediate Similarity	NPC115808
0.8304	Intermediate Similarity	NPC477137
0.8304	Intermediate Similarity	NPC219112
0.8304	Intermediate Similarity	NPC92

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 NPC138942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1070
0.2-0.3	1112
0.3-0.4	2850
0.4-0.5	1985
0.5-0.6	1207
0.6-0.7	522
0.7-0.8	100
0.8-0.85	6
0.85-0.9	10
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD3020	Approved
0.9175	High Similarity	NPD2860	Approved
0.9175	High Similarity	NPD2859	Approved
0.9072	High Similarity	NPD2934	Approved
0.9072	High Similarity	NPD2933	Approved
0.8788	High Similarity	NPD1809	Phase 2
0.8785	High Similarity	NPD7635	Approved
0.8776	High Similarity	NPD845	Approved
0.8687	High Similarity	NPD1432	Clinical (unspecified phase)
0.8505	High Similarity	NPD3021	Approved
0.8505	High Similarity	NPD3022	Approved
0.8491	Intermediate Similarity	NPD2342	Discontinued
0.8447	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8416	Intermediate Similarity	NPD844	Approved
0.8365	Intermediate Similarity	NPD940	Approved
0.8365	Intermediate Similarity	NPD846	Approved
0.8333	Intermediate Similarity	NPD288	Approved
0.8174	Intermediate Similarity	NPD4589	Approved
0.8158	Intermediate Similarity	NPD5304	Approved
0.8158	Intermediate Similarity	NPD5303	Approved
0.8144	Intermediate Similarity	NPD111	Approved
0.8051	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD2229	Approved
0.8036	Intermediate Similarity	NPD2228	Approved
0.8036	Intermediate Similarity	NPD2234	Approved
0.8018	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4750	Phase 3
0.7925	Intermediate Similarity	NPD3028	Approved
0.7925	Intermediate Similarity	NPD1242	Phase 1
0.7876	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2286	Discontinued
0.7845	Intermediate Similarity	NPD3091	Approved
0.7826	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD497	Approved
0.7778	Intermediate Similarity	NPD4093	Discontinued
0.7739	Intermediate Similarity	NPD6671	Approved
0.7719	Intermediate Similarity	NPD496	Approved
0.7719	Intermediate Similarity	NPD495	Approved
0.7719	Intermediate Similarity	NPD498	Approved
0.7712	Intermediate Similarity	NPD2932	Approved
0.7712	Intermediate Similarity	NPD3019	Approved
0.7712	Intermediate Similarity	NPD4059	Approved
0.7692	Intermediate Similarity	NPD7330	Discontinued
0.7679	Intermediate Similarity	NPD1792	Phase 2
0.7623	Intermediate Similarity	NPD1164	Approved
0.7615	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD3092	Approved
0.7568	Intermediate Similarity	NPD1445	Approved
0.7568	Intermediate Similarity	NPD1444	Approved
0.7563	Intermediate Similarity	NPD4626	Approved
0.752	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2861	Phase 2
0.748	Intermediate Similarity	NPD4060	Phase 1
0.748	Intermediate Similarity	NPD3094	Phase 2
0.7479	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4908	Phase 1
0.7438	Intermediate Similarity	NPD1610	Phase 2
0.7417	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3095	Discontinued
0.7417	Intermediate Similarity	NPD1751	Approved
0.7414	Intermediate Similarity	NPD5283	Phase 1
0.7411	Intermediate Similarity	NPD968	Approved
0.7395	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD9610	Approved
0.7387	Intermediate Similarity	NPD9608	Approved
0.7368	Intermediate Similarity	NPD5451	Approved
0.7355	Intermediate Similarity	NPD3143	Discontinued
0.7339	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1651	Approved
0.7317	Intermediate Similarity	NPD1669	Approved
0.7297	Intermediate Similarity	NPD9500	Approved
0.7295	Intermediate Similarity	NPD1201	Approved
0.7288	Intermediate Similarity	NPD709	Approved
0.7288	Intermediate Similarity	NPD6387	Discontinued
0.7281	Intermediate Similarity	NPD2684	Approved
0.7273	Intermediate Similarity	NPD2668	Approved
0.7273	Intermediate Similarity	NPD2667	Approved
0.7266	Intermediate Similarity	NPD6407	Approved
0.7266	Intermediate Similarity	NPD6405	Approved
0.7265	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1283	Approved
0.725	Intermediate Similarity	NPD1548	Phase 1
0.7248	Intermediate Similarity	NPD9273	Approved
0.7241	Intermediate Similarity	NPD228	Approved
0.7236	Intermediate Similarity	NPD3070	Discontinued
0.7236	Intermediate Similarity	NPD2232	Approved
0.7236	Intermediate Similarity	NPD2233	Approved
0.7236	Intermediate Similarity	NPD2230	Approved
0.7227	Intermediate Similarity	NPD7636	Approved
0.7222	Intermediate Similarity	NPD5736	Approved
0.7213	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4103	Phase 2
0.72	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2935	Discontinued
0.719	Intermediate Similarity	NPD5691	Approved
0.7179	Intermediate Similarity	NPD5535	Approved
0.7177	Intermediate Similarity	NPD4659	Approved
0.7177	Intermediate Similarity	NPD6583	Phase 3
0.7177	Intermediate Similarity	NPD6582	Phase 2
0.7154	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1611	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD2194	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD2195	Approved
0.712	Intermediate Similarity	NPD6696	Suspended
0.7119	Intermediate Similarity	NPD1398	Phase 1
0.7117	Intermediate Similarity	NPD1616	Discontinued
0.7111	Intermediate Similarity	NPD3400	Discontinued
0.7109	Intermediate Similarity	NPD3027	Phase 3
0.7109	Intermediate Similarity	NPD5155	Approved
0.7109	Intermediate Similarity	NPD5156	Approved
0.7099	Intermediate Similarity	NPD4097	Suspended
0.7097	Intermediate Similarity	NPD2561	Approved
0.7097	Intermediate Similarity	NPD2562	Approved
0.7087	Intermediate Similarity	NPD3637	Approved
0.7087	Intermediate Similarity	NPD3635	Approved
0.7087	Intermediate Similarity	NPD3636	Approved
0.7087	Intermediate Similarity	NPD4208	Discontinued
0.7083	Intermediate Similarity	NPD7340	Approved
0.7073	Intermediate Similarity	NPD3421	Phase 3
0.7073	Intermediate Similarity	NPD3847	Discontinued
0.7073	Intermediate Similarity	NPD3023	Approved
0.7073	Intermediate Similarity	NPD3026	Approved
0.7071	Intermediate Similarity	NPD9088	Approved
0.7069	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5404	Approved
0.7068	Intermediate Similarity	NPD5405	Approved
0.7068	Intermediate Similarity	NPD5406	Approved
0.7068	Intermediate Similarity	NPD5408	Approved
0.7063	Intermediate Similarity	NPD1131	Approved
0.7063	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD1129	Approved
0.7063	Intermediate Similarity	NPD1133	Approved
0.7063	Intermediate Similarity	NPD3055	Approved
0.7063	Intermediate Similarity	NPD1470	Approved
0.7063	Intermediate Similarity	NPD1135	Approved
0.7063	Intermediate Similarity	NPD1134	Approved
0.7063	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD475	Phase 2
0.7059	Intermediate Similarity	NPD1791	Approved
0.7059	Intermediate Similarity	NPD1793	Approved
0.7049	Intermediate Similarity	NPD3024	Approved
0.7049	Intermediate Similarity	NPD3025	Approved
0.7045	Intermediate Similarity	NPD3552	Approved
0.7045	Intermediate Similarity	NPD3555	Approved
0.7045	Intermediate Similarity	NPD3554	Approved
0.7045	Intermediate Similarity	NPD3553	Approved
0.704	Intermediate Similarity	NPD4749	Approved
0.7034	Intermediate Similarity	NPD7843	Approved
0.7034	Intermediate Similarity	NPD9379	Approved
0.7034	Intermediate Similarity	NPD1138	Approved
0.7034	Intermediate Similarity	NPD9377	Approved
0.7031	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2606	Approved
0.7031	Intermediate Similarity	NPD2605	Approved
0.7016	Intermediate Similarity	NPD1281	Approved
0.701	Intermediate Similarity	NPD9087	Approved
0.7008	Intermediate Similarity	NPD4624	Approved
0.7008	Intermediate Similarity	NPD3691	Phase 2
0.7008	Intermediate Similarity	NPD3690	Phase 2
0.7	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD256	Approved
0.7	Intermediate Similarity	NPD255	Approved
0.6992	Remote Similarity	NPD2799	Discontinued
0.6985	Remote Similarity	NPD7003	Approved
0.6984	Remote Similarity	NPD5311	Approved
0.6984	Remote Similarity	NPD5310	Approved
0.6984	Remote Similarity	NPD8651	Approved
0.6957	Remote Similarity	NPD2421	Approved
0.6957	Remote Similarity	NPD7390	Discontinued
0.6957	Remote Similarity	NPD2420	Approved
0.6953	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4212	Discontinued
0.6949	Remote Similarity	NPD1137	Approved
0.6949	Remote Similarity	NPD1139	Approved
0.6942	Remote Similarity	NPD405	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4477	Approved
0.694	Remote Similarity	NPD4476	Approved
0.6935	Remote Similarity	NPD1980	Approved
0.6935	Remote Similarity	NPD1983	Approved
0.6935	Remote Similarity	NPD1981	Approved
0.6923	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9618	Approved
0.6917	Remote Similarity	NPD9614	Approved
0.6912	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3445	Approved
0.6911	Remote Similarity	NPD3444	Approved
0.6911	Remote Similarity	NPD3443	Approved
0.6905	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4818	Approved
0.6903	Remote Similarity	NPD4817	Approved
0.6899	Remote Similarity	NPD3594	Approved
0.6899	Remote Similarity	NPD3595	Approved
0.6899	Remote Similarity	NPD4207	Discontinued
0.6897	Remote Similarity	NPD290	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