NPASS Compound

Structure

NPC12656 OpenBabel07101719242D 22 23 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 3 4 1 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 2 1 6 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.14
Volume:	319.477
LogP:	3.404
LogD:	2.543
LogS:	-3.151
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	3.269
Fsp3:	0.222
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:	-4.722
MDCK Permeability:	8.192094355763402e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	97.79015350341797%
Volume Distribution (VD):	0.627
Pgp-substrate:	1.2775673866271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.687
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.293
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.427
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.844
CYP2D6-substrate:	0.811
CYP3A4-inhibitor:	0.327
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	5.086
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.38
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.218
Skin Sensitization:	0.526
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.465
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC12656

Natural Product ID:	NPC12656
*Common Name:**	Strebluslignanol
IUPAC Name:	(1R,2R)-1-[4-hydroxy-3-(2-hydroxy-5-prop-2-enylphenyl)phenyl]propane-1,2-diol
Synonyms:	strebluslignanol
Standard InCHIKey:	PCEGAFMZBXEUGY-ZMZPIMSZSA-N
Standard InCHI:	InChI=1S/C18H20O4/c1-3-4-12-5-7-16(20)14(9-12)15-10-13(6-8-17(15)21)18(22)11(2)19/h3,5-11,18-22H,1,4H2,2H3/t11-,18+/m1/s1
SMILES:	C=CCc1ccc(c(c1)c1cc(ccc1O)[C@H]([C@H](O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346747
PubChem CID:	71717736
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
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Others	2

Activity Type	# Activity
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	1000000.0	nM	PMID[500650]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.36	n.a.	PMID[500650]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	147160.0	nM	PMID[500650]
NPT27	Others	Unspecified		CC50	=	200070.0	nM	PMID[500650]

☑ 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 NPC12656 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	264
0.1-0.2	1346
0.2-0.3	3353
0.3-0.4	11237
0.4-0.5	8481
0.5-0.6	7180
0.6-0.7	8092
0.7-0.8	2466
0.8-0.85	216
0.85-0.9	51
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9813	High Similarity	NPC473137
0.9717	High Similarity	NPC308689
0.9623	High Similarity	NPC44732
0.9434	High Similarity	NPC262365
0.9151	High Similarity	NPC138942
0.9123	High Similarity	NPC223451
0.9057	High Similarity	NPC288411
0.8962	High Similarity	NPC168829
0.8824	High Similarity	NPC127975
0.8803	High Similarity	NPC31936
0.8793	High Similarity	NPC475245
0.8761	High Similarity	NPC120280
0.875	High Similarity	NPC228425
0.8739	High Similarity	NPC296683
0.8739	High Similarity	NPC475018
0.8727	High Similarity	NPC95344
0.8707	High Similarity	NPC182240
0.8692	High Similarity	NPC91461
0.8692	High Similarity	NPC7686
0.8692	High Similarity	NPC40258
0.8684	High Similarity	NPC474486
0.8679	High Similarity	NPC78119
0.8679	High Similarity	NPC216468
0.8679	High Similarity	NPC132078
0.8679	High Similarity	NPC51333
0.8679	High Similarity	NPC128723
0.8649	High Similarity	NPC473524
0.8632	High Similarity	NPC473136
0.8624	High Similarity	NPC99557
0.8624	High Similarity	NPC219286
0.8621	High Similarity	NPC469609
0.8618	High Similarity	NPC143483
0.8598	High Similarity	NPC213730
0.8584	High Similarity	NPC43525
0.8584	High Similarity	NPC228988
0.8583	High Similarity	NPC231767
0.8571	High Similarity	NPC226401
0.8571	High Similarity	NPC174096
0.8571	High Similarity	NPC79793
0.8571	High Similarity	NPC147634
0.8571	High Similarity	NPC120982
0.8559	High Similarity	NPC61885
0.8559	High Similarity	NPC63698
0.8547	High Similarity	NPC469644
0.8547	High Similarity	NPC151197
0.8545	High Similarity	NPC54765
0.8545	High Similarity	NPC271274
0.8534	High Similarity	NPC476266
0.8532	High Similarity	NPC323810
0.8509	High Similarity	NPC141003
0.8509	High Similarity	NPC35344
0.8509	High Similarity	NPC471485
0.8496	Intermediate Similarity	NPC257430
0.8496	Intermediate Similarity	NPC179002
0.8496	Intermediate Similarity	NPC95716
0.8496	Intermediate Similarity	NPC187583
0.8496	Intermediate Similarity	NPC165770
0.8496	Intermediate Similarity	NPC225679
0.8496	Intermediate Similarity	NPC151537
0.8496	Intermediate Similarity	NPC4493
0.8496	Intermediate Similarity	NPC476632
0.8482	Intermediate Similarity	NPC55617
0.8482	Intermediate Similarity	NPC62258
0.8462	Intermediate Similarity	NPC471671
0.8455	Intermediate Similarity	NPC472968
0.8455	Intermediate Similarity	NPC471064
0.8455	Intermediate Similarity	NPC154899
0.8455	Intermediate Similarity	NPC233396
0.8448	Intermediate Similarity	NPC301651
0.8448	Intermediate Similarity	NPC308828
0.8448	Intermediate Similarity	NPC473556
0.8435	Intermediate Similarity	NPC107240
0.8426	Intermediate Similarity	NPC225506
0.8426	Intermediate Similarity	NPC294741
0.8421	Intermediate Similarity	NPC286222
0.8421	Intermediate Similarity	NPC46940
0.8417	Intermediate Similarity	NPC471794
0.8411	Intermediate Similarity	NPC77492
0.8407	Intermediate Similarity	NPC132720
0.8396	Intermediate Similarity	NPC26244
0.8396	Intermediate Similarity	NPC313650
0.8378	Intermediate Similarity	NPC92623
0.8378	Intermediate Similarity	NPC135464
0.8376	Intermediate Similarity	NPC277588
0.8376	Intermediate Similarity	NPC304510
0.8376	Intermediate Similarity	NPC172219
0.8376	Intermediate Similarity	NPC477136
0.8376	Intermediate Similarity	NPC320864
0.8374	Intermediate Similarity	NPC21563
0.8362	Intermediate Similarity	NPC147179
0.8361	Intermediate Similarity	NPC81641
0.8349	Intermediate Similarity	NPC471578
0.8349	Intermediate Similarity	NPC101025
0.8348	Intermediate Similarity	NPC176730
0.8348	Intermediate Similarity	NPC123175
0.8348	Intermediate Similarity	NPC117846
0.8348	Intermediate Similarity	NPC261343
0.8347	Intermediate Similarity	NPC474160
0.8333	Intermediate Similarity	NPC122005
0.8333	Intermediate Similarity	NPC252821
0.8333	Intermediate Similarity	NPC237667
0.8333	Intermediate Similarity	NPC92730
0.8319	Intermediate Similarity	NPC472071
0.8319	Intermediate Similarity	NPC254833
0.8319	Intermediate Similarity	NPC58865
0.8319	Intermediate Similarity	NPC228343
0.8318	Intermediate Similarity	NPC473388
0.8318	Intermediate Similarity	NPC82664
0.8318	Intermediate Similarity	NPC216520
0.8318	Intermediate Similarity	NPC292730
0.8318	Intermediate Similarity	NPC132271
0.8305	Intermediate Similarity	NPC154030
0.8305	Intermediate Similarity	NPC9592
0.8305	Intermediate Similarity	NPC48781
0.8302	Intermediate Similarity	NPC151715
0.8302	Intermediate Similarity	NPC128062
0.8291	Intermediate Similarity	NPC219112
0.8291	Intermediate Similarity	NPC92
0.8291	Intermediate Similarity	NPC308311
0.8291	Intermediate Similarity	NPC477137
0.8291	Intermediate Similarity	NPC469663
0.8291	Intermediate Similarity	NPC38893
0.8288	Intermediate Similarity	NPC474839
0.8281	Intermediate Similarity	NPC256262
0.8276	Intermediate Similarity	NPC268160
0.8268	Intermediate Similarity	NPC170185
0.8264	Intermediate Similarity	NPC150026
0.8264	Intermediate Similarity	NPC71094
0.8261	Intermediate Similarity	NPC153795
0.8261	Intermediate Similarity	NPC290353
0.8261	Intermediate Similarity	NPC42911
0.8254	Intermediate Similarity	NPC103799
0.825	Intermediate Similarity	NPC24125
0.8246	Intermediate Similarity	NPC63345
0.8241	Intermediate Similarity	NPC225464
0.8241	Intermediate Similarity	NPC474073
0.8235	Intermediate Similarity	NPC176893
0.8235	Intermediate Similarity	NPC191866
0.8226	Intermediate Similarity	NPC476536
0.8224	Intermediate Similarity	NPC8392
0.822	Intermediate Similarity	NPC299180
0.822	Intermediate Similarity	NPC470760
0.8214	Intermediate Similarity	NPC248904
0.8208	Intermediate Similarity	NPC138117
0.8208	Intermediate Similarity	NPC325292
0.8208	Intermediate Similarity	NPC271440
0.8205	Intermediate Similarity	NPC192948
0.8205	Intermediate Similarity	NPC35797
0.8203	Intermediate Similarity	NPC184269
0.8198	Intermediate Similarity	NPC475225
0.8198	Intermediate Similarity	NPC119860
0.8197	Intermediate Similarity	NPC473451
0.8197	Intermediate Similarity	NPC53567
0.819	Intermediate Similarity	NPC715
0.8182	Intermediate Similarity	NPC475166
0.8182	Intermediate Similarity	NPC51015
0.8182	Intermediate Similarity	NPC251259
0.8167	Intermediate Similarity	NPC68339
0.816	Intermediate Similarity	NPC148366
0.816	Intermediate Similarity	NPC311293
0.816	Intermediate Similarity	NPC274717
0.8158	Intermediate Similarity	NPC306045
0.8158	Intermediate Similarity	NPC265211
0.8151	Intermediate Similarity	NPC144343
0.8145	Intermediate Similarity	NPC470724
0.8142	Intermediate Similarity	NPC151477
0.814	Intermediate Similarity	NPC79957
0.8136	Intermediate Similarity	NPC474358
0.8136	Intermediate Similarity	NPC257540
0.8136	Intermediate Similarity	NPC137496
0.8136	Intermediate Similarity	NPC474387
0.8136	Intermediate Similarity	NPC154511
0.8136	Intermediate Similarity	NPC148055
0.8136	Intermediate Similarity	NPC247858
0.8136	Intermediate Similarity	NPC115808
0.813	Intermediate Similarity	NPC224342
0.8125	Intermediate Similarity	NPC474453
0.8125	Intermediate Similarity	NPC471350
0.812	Intermediate Similarity	NPC195922
0.8113	Intermediate Similarity	NPC204210
0.8113	Intermediate Similarity	NPC45040
0.8108	Intermediate Similarity	NPC235762
0.8108	Intermediate Similarity	NPC471228
0.8108	Intermediate Similarity	NPC108497
0.8103	Intermediate Similarity	NPC302371
0.8103	Intermediate Similarity	NPC166995
0.8103	Intermediate Similarity	NPC473521
0.8099	Intermediate Similarity	NPC160854
0.8099	Intermediate Similarity	NPC131868
0.8099	Intermediate Similarity	NPC328504
0.8099	Intermediate Similarity	NPC469703
0.8099	Intermediate Similarity	NPC469704
0.8099	Intermediate Similarity	NPC201402
0.8091	Intermediate Similarity	NPC130103
0.8091	Intermediate Similarity	NPC174911
0.8087	Intermediate Similarity	NPC13482
0.8083	Intermediate Similarity	NPC109371
0.8083	Intermediate Similarity	NPC470215
0.8083	Intermediate Similarity	NPC217174
0.8083	Intermediate Similarity	NPC470214

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 NPC12656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	840
0.2-0.3	1421
0.3-0.4	2846
0.4-0.5	1950
0.5-0.6	1157
0.6-0.7	575
0.7-0.8	94
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8505	High Similarity	NPD3020	Approved
0.8396	Intermediate Similarity	NPD2859	Approved
0.8396	Intermediate Similarity	NPD2860	Approved
0.8319	Intermediate Similarity	NPD3022	Approved
0.8319	Intermediate Similarity	NPD3021	Approved
0.8302	Intermediate Similarity	NPD2934	Approved
0.8302	Intermediate Similarity	NPD2933	Approved
0.8103	Intermediate Similarity	NPD7635	Approved
0.8065	Intermediate Similarity	NPD3094	Phase 2
0.8056	Intermediate Similarity	NPD1809	Phase 2
0.8037	Intermediate Similarity	NPD845	Approved
0.8033	Intermediate Similarity	NPD3092	Approved
0.8018	Intermediate Similarity	NPD940	Approved
0.8018	Intermediate Similarity	NPD846	Approved
0.7963	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD3091	Approved
0.7826	Intermediate Similarity	NPD2342	Discontinued
0.7812	Intermediate Similarity	NPD3027	Phase 3
0.7768	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD844	Approved
0.7724	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4750	Phase 3
0.7692	Intermediate Similarity	NPD6405	Approved
0.7692	Intermediate Similarity	NPD6407	Approved
0.7658	Intermediate Similarity	NPD288	Approved
0.7656	Intermediate Similarity	NPD2861	Phase 2
0.7634	Intermediate Similarity	NPD4060	Phase 1
0.7632	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD1242	Phase 1
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7581	Intermediate Similarity	NPD3095	Discontinued
0.7581	Intermediate Similarity	NPD4589	Approved
0.7574	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5303	Approved
0.7561	Intermediate Similarity	NPD5304	Approved
0.7559	Intermediate Similarity	NPD8651	Approved
0.7518	Intermediate Similarity	NPD3400	Discontinued
0.75	Intermediate Similarity	NPD4103	Phase 2
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.748	Intermediate Similarity	NPD4659	Approved
0.7463	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4538	Approved
0.7463	Intermediate Similarity	NPD4536	Approved
0.746	Intermediate Similarity	NPD1610	Phase 2
0.7459	Intermediate Similarity	NPD7157	Approved
0.7458	Intermediate Similarity	NPD2684	Approved
0.7456	Intermediate Similarity	NPD3028	Approved
0.7453	Intermediate Similarity	NPD111	Approved
0.7438	Intermediate Similarity	NPD2228	Approved
0.7438	Intermediate Similarity	NPD2229	Approved
0.7438	Intermediate Similarity	NPD2234	Approved
0.7402	Intermediate Similarity	NPD2561	Approved
0.7402	Intermediate Similarity	NPD2562	Approved
0.7398	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD497	Approved
0.7368	Intermediate Similarity	NPD3062	Approved
0.7368	Intermediate Similarity	NPD3059	Approved
0.7368	Intermediate Similarity	NPD3061	Approved
0.7364	Intermediate Similarity	NPD1129	Approved
0.7364	Intermediate Similarity	NPD1133	Approved
0.7364	Intermediate Similarity	NPD1134	Approved
0.7364	Intermediate Similarity	NPD1135	Approved
0.7364	Intermediate Similarity	NPD1131	Approved
0.7355	Intermediate Similarity	NPD7843	Approved
0.7333	Intermediate Similarity	NPD3552	Approved
0.7333	Intermediate Similarity	NPD3553	Approved
0.7333	Intermediate Similarity	NPD3554	Approved
0.7333	Intermediate Similarity	NPD3555	Approved
0.7302	Intermediate Similarity	NPD5126	Approved
0.7302	Intermediate Similarity	NPD5125	Phase 3
0.7302	Intermediate Similarity	NPD2286	Discontinued
0.7302	Intermediate Similarity	NPD9381	Approved
0.7302	Intermediate Similarity	NPD9384	Approved
0.7299	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD498	Approved
0.7295	Intermediate Similarity	NPD495	Approved
0.7295	Intermediate Similarity	NPD496	Approved
0.7295	Intermediate Similarity	NPD5283	Phase 1
0.728	Intermediate Similarity	NPD1548	Phase 1
0.7279	Intermediate Similarity	NPD5960	Phase 3
0.7279	Intermediate Similarity	NPD5588	Approved
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7259	Intermediate Similarity	NPD5314	Approved
0.7236	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD290	Approved
0.7222	Intermediate Similarity	NPD4093	Discontinued
0.7209	Intermediate Similarity	NPD9622	Approved
0.72	Intermediate Similarity	NPD16	Approved
0.72	Intermediate Similarity	NPD856	Approved
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1091	Approved
0.7185	Intermediate Similarity	NPD6355	Discontinued
0.7183	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6671	Approved
0.7174	Intermediate Similarity	NPD7266	Discontinued
0.7165	Intermediate Similarity	NPD4059	Approved
0.7165	Intermediate Similarity	NPD4626	Approved
0.7165	Intermediate Similarity	NPD3019	Approved
0.7165	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD7330	Discontinued
0.7132	Intermediate Similarity	NPD2568	Approved
0.7131	Intermediate Similarity	NPD228	Approved
0.7121	Intermediate Similarity	NPD5736	Approved
0.7121	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3620	Phase 2
0.7111	Intermediate Similarity	NPD2238	Phase 2
0.7111	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1792	Phase 2
0.7099	Intermediate Similarity	NPD1164	Approved
0.709	Intermediate Similarity	NPD6798	Discontinued
0.7063	Intermediate Similarity	NPD317	Approved
0.7063	Intermediate Similarity	NPD318	Approved
0.7059	Intermediate Similarity	NPD5735	Approved
0.7055	Intermediate Similarity	NPD4380	Phase 2
0.7054	Intermediate Similarity	NPD1201	Approved
0.705	Intermediate Similarity	NPD5762	Approved
0.705	Intermediate Similarity	NPD5763	Approved
0.7049	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9619	Approved
0.7045	Intermediate Similarity	NPD9621	Approved
0.7045	Intermediate Similarity	NPD9620	Approved
0.7045	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5058	Phase 3
0.7031	Intermediate Similarity	NPD6516	Phase 2
0.7031	Intermediate Similarity	NPD5846	Approved
0.7021	Intermediate Similarity	NPD4628	Phase 3
0.7008	Intermediate Similarity	NPD7741	Discontinued
0.7	Intermediate Similarity	NPD1445	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD1444	Approved
0.6985	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5408	Approved
0.6978	Remote Similarity	NPD5404	Approved
0.6978	Remote Similarity	NPD5406	Approved
0.6978	Remote Similarity	NPD2935	Discontinued
0.6978	Remote Similarity	NPD5405	Approved
0.697	Remote Similarity	NPD1470	Approved
0.6967	Remote Similarity	NPD5451	Approved
0.6963	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD601	Approved
0.6963	Remote Similarity	NPD598	Approved
0.6963	Remote Similarity	NPD597	Approved
0.696	Remote Similarity	NPD9614	Approved
0.696	Remote Similarity	NPD9618	Approved
0.6953	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5691	Approved
0.6953	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1651	Approved
0.6947	Remote Similarity	NPD1669	Approved
0.6947	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6583	Phase 3
0.6947	Remote Similarity	NPD6582	Phase 2
0.6944	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6666	Approved
0.6923	Remote Similarity	NPD6667	Approved
0.6917	Remote Similarity	NPD6584	Phase 3
0.6917	Remote Similarity	NPD3691	Phase 2
0.6917	Remote Similarity	NPD3690	Phase 2
0.6913	Remote Similarity	NPD8455	Phase 2
0.6913	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1136	Approved
0.6912	Remote Similarity	NPD1132	Approved
0.6912	Remote Similarity	NPD6663	Approved
0.6912	Remote Similarity	NPD1130	Approved
0.6905	Remote Similarity	NPD6387	Discontinued
0.6901	Remote Similarity	NPD4535	Phase 3
0.6899	Remote Similarity	NPD1751	Approved
0.6899	Remote Similarity	NPD2667	Approved
0.6899	Remote Similarity	NPD2668	Approved
0.6894	Remote Similarity	NPD1283	Approved
0.6894	Remote Similarity	NPD6696	Suspended
0.6884	Remote Similarity	NPD823	Approved
0.6884	Remote Similarity	NPD817	Approved
0.6875	Remote Similarity	NPD7390	Discontinued
0.6875	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7041	Phase 2
0.687	Remote Similarity	NPD2230	Approved
0.687	Remote Similarity	NPD2233	Approved
0.687	Remote Similarity	NPD2232	Approved
0.6866	Remote Similarity	NPD4208	Discontinued
0.6861	Remote Similarity	NPD943	Approved
0.6861	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2677	Approved
0.6846	Remote Similarity	NPD3143	Discontinued
0.6846	Remote Similarity	NPD3421	Phase 3
0.6846	Remote Similarity	NPD3847	Discontinued
0.6842	Remote Similarity	NPD3055	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