NPASS Compound

Structure

NPC297657 OpenBabel07101718242D 24 25 0 0 0 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 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 -6.9282 1.0000 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 -6.9282 0.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 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 -7.7942 1.5000 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 2 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 15 20 2 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	340.29
LogP:	2.873
LogD:	2.956
LogS:	-3.025
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	2.602
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.016
MDCK Permeability:	1.513814913778333e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.079

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	100.18761444091797%
Volume Distribution (VD):	0.35
Pgp-substrate:	0.6337243318557739%

ADMET: Metabolism

CYP1A2-inhibitor:	0.541
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.294
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.632
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.212
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.484
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	17.379
Half-life (T1/2):	0.947

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.239
Rat Oral Acute Toxicity:	0.601
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.98
Carcinogencity:	0.558
Eye Corrosion:	0.089
Eye Irritation:	0.954
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC297657

Natural Product ID:	NPC297657
*Common Name:**	(1E,4E)-1,7-Bis(3,4-Dihydroxyphenyl)Hepta-1,4-Dien-3-One
IUPAC Name:	(1E,4E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,4-dien-3-one
Synonyms:
Standard InCHIKey:	BQXWNGCLBOSNPN-MSGXFJBMSA-N
Standard InCHI:	InChI=1S/C19H18O5/c20-15(8-5-14-7-10-17(22)19(24)12-14)4-2-1-3-13-6-9-16(21)18(23)11-13/h2,4-12,21-24H,1,3H2/b4-2+,8-5+
SMILES:	O=C(/C=C/c1ccc(c(c1)O)O)/C=C/CCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346807
PubChem CID:	56950212
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	36.5	%	PMID[569756]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	66.5	%	PMID[569756]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	86.5	%	PMID[569756]

☑ 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 NPC297657 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	290
0.1-0.2	1749
0.2-0.3	4749
0.3-0.4	13792
0.4-0.5	4863
0.5-0.6	7519
0.6-0.7	7556
0.7-0.8	1943
0.8-0.85	166
0.85-0.9	53
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC61062
0.9537	High Similarity	NPC299252
0.9537	High Similarity	NPC277394
0.9528	High Similarity	NPC51698
0.9135	High Similarity	NPC471511
0.9135	High Similarity	NPC52087
0.9135	High Similarity	NPC79672
0.9107	High Similarity	NPC141791
0.9107	High Similarity	NPC263386
0.9099	High Similarity	NPC278652
0.9065	High Similarity	NPC254833
0.9065	High Similarity	NPC228343
0.9029	High Similarity	NPC223393
0.8981	High Similarity	NPC120982
0.8981	High Similarity	NPC174096
0.8981	High Similarity	NPC79793
0.8981	High Similarity	NPC147634
0.8981	High Similarity	NPC226401
0.8962	High Similarity	NPC1075
0.8962	High Similarity	NPC294902
0.8962	High Similarity	NPC1786
0.8957	High Similarity	NPC86900
0.8947	High Similarity	NPC470849
0.8947	High Similarity	NPC470848
0.8932	High Similarity	NPC130193
0.8899	High Similarity	NPC257430
0.8899	High Similarity	NPC187583
0.8899	High Similarity	NPC179002
0.8889	High Similarity	NPC55617
0.8889	High Similarity	NPC62258
0.887	High Similarity	NPC147654
0.8868	High Similarity	NPC239291
0.8857	High Similarity	NPC196479
0.885	High Similarity	NPC275519
0.8835	High Similarity	NPC109955
0.8835	High Similarity	NPC201967
0.8785	High Similarity	NPC19149
0.8783	High Similarity	NPC224814
0.8783	High Similarity	NPC236520
0.8783	High Similarity	NPC189844
0.8783	High Similarity	NPC269843
0.8783	High Similarity	NPC14007
0.8783	High Similarity	NPC109083
0.8783	High Similarity	NPC60962
0.8783	High Similarity	NPC294361
0.8761	High Similarity	NPC200988
0.8761	High Similarity	NPC175799
0.8761	High Similarity	NPC610
0.8761	High Similarity	NPC145023
0.8696	High Similarity	NPC265454
0.8696	High Similarity	NPC34634
0.8684	High Similarity	NPC203124
0.8684	High Similarity	NPC86198
0.8684	High Similarity	NPC309434
0.8679	High Similarity	NPC135784
0.8679	High Similarity	NPC68269
0.8661	High Similarity	NPC120280
0.8624	High Similarity	NPC233835
0.8621	High Similarity	NPC98305
0.8611	High Similarity	NPC70843
0.8611	High Similarity	NPC95178
0.8611	High Similarity	NPC477814
0.8611	High Similarity	NPC29989
0.8611	High Similarity	NPC69332
0.8609	High Similarity	NPC70084
0.8609	High Similarity	NPC470214
0.8609	High Similarity	NPC109371
0.8609	High Similarity	NPC470215
0.8585	High Similarity	NPC110764
0.8583	High Similarity	NPC123228
0.8583	High Similarity	NPC151167
0.8583	High Similarity	NPC123722
0.8583	High Similarity	NPC276466
0.8583	High Similarity	NPC5018
0.8559	High Similarity	NPC470355
0.8559	High Similarity	NPC106659
0.8559	High Similarity	NPC268032
0.8559	High Similarity	NPC160900
0.8559	High Similarity	NPC18984
0.8559	High Similarity	NPC229084
0.8559	High Similarity	NPC226250
0.8545	High Similarity	NPC88141
0.8509	High Similarity	NPC281277
0.85	High Similarity	NPC213552
0.85	High Similarity	NPC84076
0.85	High Similarity	NPC90128
0.85	High Similarity	NPC120225
0.85	High Similarity	NPC303680
0.85	High Similarity	NPC179777
0.8496	Intermediate Similarity	NPC33749
0.8496	Intermediate Similarity	NPC261453
0.8496	Intermediate Similarity	NPC328593
0.8482	Intermediate Similarity	NPC131530
0.8468	Intermediate Similarity	NPC222084
0.8462	Intermediate Similarity	NPC107522
0.8462	Intermediate Similarity	NPC274678
0.8455	Intermediate Similarity	NPC34864
0.8455	Intermediate Similarity	NPC105727
0.8455	Intermediate Similarity	NPC58427
0.8455	Intermediate Similarity	NPC114392
0.8443	Intermediate Similarity	NPC304622
0.8435	Intermediate Similarity	NPC150919
0.8435	Intermediate Similarity	NPC280001
0.8426	Intermediate Similarity	NPC12278
0.8426	Intermediate Similarity	NPC120719
0.8421	Intermediate Similarity	NPC474967
0.8421	Intermediate Similarity	NPC233669
0.8417	Intermediate Similarity	NPC87113
0.8417	Intermediate Similarity	NPC197832
0.8417	Intermediate Similarity	NPC289459
0.8407	Intermediate Similarity	NPC95381
0.8407	Intermediate Similarity	NPC471485
0.8403	Intermediate Similarity	NPC306100
0.8403	Intermediate Similarity	NPC212541
0.8403	Intermediate Similarity	NPC285345
0.8396	Intermediate Similarity	NPC131587
0.839	Intermediate Similarity	NPC472271
0.8365	Intermediate Similarity	NPC151715
0.8365	Intermediate Similarity	NPC76938
0.8364	Intermediate Similarity	NPC176527
0.8362	Intermediate Similarity	NPC470626
0.8362	Intermediate Similarity	NPC144343
0.8347	Intermediate Similarity	NPC276014
0.8333	Intermediate Similarity	NPC288945
0.8333	Intermediate Similarity	NPC246704
0.8333	Intermediate Similarity	NPC217472
0.8319	Intermediate Similarity	NPC286573
0.8304	Intermediate Similarity	NPC183700
0.8293	Intermediate Similarity	NPC83062
0.8291	Intermediate Similarity	NPC217174
0.8291	Intermediate Similarity	NPC268572
0.8286	Intermediate Similarity	NPC32714
0.8286	Intermediate Similarity	NPC26244
0.8279	Intermediate Similarity	NPC156539
0.8279	Intermediate Similarity	NPC107672
0.8276	Intermediate Similarity	NPC293619
0.8276	Intermediate Similarity	NPC86947
0.8276	Intermediate Similarity	NPC277588
0.8273	Intermediate Similarity	NPC188677
0.8269	Intermediate Similarity	NPC181709
0.8264	Intermediate Similarity	NPC257589
0.8264	Intermediate Similarity	NPC53305
0.8264	Intermediate Similarity	NPC67951
0.8257	Intermediate Similarity	NPC8931
0.8257	Intermediate Similarity	NPC120693
0.8257	Intermediate Similarity	NPC261573
0.825	Intermediate Similarity	NPC242372
0.825	Intermediate Similarity	NPC257976
0.825	Intermediate Similarity	NPC164778
0.825	Intermediate Similarity	NPC4181
0.8246	Intermediate Similarity	NPC148969
0.8246	Intermediate Similarity	NPC264558
0.8226	Intermediate Similarity	NPC244441
0.822	Intermediate Similarity	NPC227217
0.822	Intermediate Similarity	NPC117780
0.822	Intermediate Similarity	NPC232316
0.822	Intermediate Similarity	NPC95614
0.822	Intermediate Similarity	NPC475245
0.822	Intermediate Similarity	NPC242885
0.822	Intermediate Similarity	NPC165133
0.822	Intermediate Similarity	NPC56214
0.8211	Intermediate Similarity	NPC478215
0.8211	Intermediate Similarity	NPC234175
0.8211	Intermediate Similarity	NPC110313
0.8208	Intermediate Similarity	NPC82664
0.8208	Intermediate Similarity	NPC216520
0.8208	Intermediate Similarity	NPC473388
0.8208	Intermediate Similarity	NPC132271
0.8208	Intermediate Similarity	NPC292730
0.8205	Intermediate Similarity	NPC122009
0.8197	Intermediate Similarity	NPC127937
0.8197	Intermediate Similarity	NPC118584
0.8197	Intermediate Similarity	NPC92207
0.8182	Intermediate Similarity	NPC312404
0.8182	Intermediate Similarity	NPC146886
0.8182	Intermediate Similarity	NPC20443
0.8182	Intermediate Similarity	NPC273686
0.8182	Intermediate Similarity	NPC60517
0.8182	Intermediate Similarity	NPC85565
0.8174	Intermediate Similarity	NPC285350
0.8173	Intermediate Similarity	NPC45040
0.8167	Intermediate Similarity	NPC114298
0.8165	Intermediate Similarity	NPC477802
0.8165	Intermediate Similarity	NPC477801
0.816	Intermediate Similarity	NPC198388
0.8158	Intermediate Similarity	NPC228988
0.8151	Intermediate Similarity	NPC24125
0.8151	Intermediate Similarity	NPC158949
0.8151	Intermediate Similarity	NPC207613
0.8148	Intermediate Similarity	NPC294741
0.8145	Intermediate Similarity	NPC470747
0.8142	Intermediate Similarity	NPC116842
0.8142	Intermediate Similarity	NPC21162
0.8136	Intermediate Similarity	NPC191866
0.8136	Intermediate Similarity	NPC281298
0.8136	Intermediate Similarity	NPC310338
0.8131	Intermediate Similarity	NPC32674
0.812	Intermediate Similarity	NPC283468
0.812	Intermediate Similarity	NPC65791
0.8115	Intermediate Similarity	NPC3221

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 NPC297657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	1056
0.2-0.3	1305
0.3-0.4	2957
0.4-0.5	1932
0.5-0.6	1173
0.6-0.7	392
0.7-0.8	62
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9065	High Similarity	NPD3022	Approved
0.9065	High Similarity	NPD3021	Approved
0.8559	High Similarity	NPD4379	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD2933	Approved
0.8365	Intermediate Similarity	NPD2934	Approved
0.8286	Intermediate Similarity	NPD2859	Approved
0.8286	Intermediate Similarity	NPD2860	Approved
0.8224	Intermediate Similarity	NPD3020	Approved
0.7966	Intermediate Similarity	NPD5536	Phase 2
0.7953	Intermediate Similarity	NPD943	Approved
0.7913	Intermediate Similarity	NPD228	Approved
0.7845	Intermediate Similarity	NPD9379	Approved
0.7845	Intermediate Similarity	NPD9377	Approved
0.7818	Intermediate Similarity	NPD1242	Phase 1
0.7742	Intermediate Similarity	NPD5311	Approved
0.7742	Intermediate Similarity	NPD5310	Approved
0.7727	Intermediate Similarity	NPD7266	Discontinued
0.7685	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3055	Approved
0.768	Intermediate Similarity	NPD3053	Approved
0.7672	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5283	Phase 1
0.7615	Intermediate Similarity	NPD844	Approved
0.7578	Intermediate Similarity	NPD3027	Phase 3
0.7556	Intermediate Similarity	NPD8166	Discontinued
0.75	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD111	Approved
0.748	Intermediate Similarity	NPD2932	Approved
0.748	Intermediate Similarity	NPD3019	Approved
0.744	Intermediate Similarity	NPD9269	Phase 2
0.744	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3061	Approved
0.7405	Intermediate Similarity	NPD3062	Approved
0.7405	Intermediate Similarity	NPD3059	Approved
0.7387	Intermediate Similarity	NPD288	Approved
0.7385	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6190	Approved
0.7364	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD258	Approved
0.7344	Intermediate Similarity	NPD257	Approved
0.7339	Intermediate Similarity	NPD9384	Approved
0.7339	Intermediate Similarity	NPD9381	Approved
0.7313	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5314	Approved
0.7287	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD9569	Approved
0.7287	Intermediate Similarity	NPD9494	Approved
0.7281	Intermediate Similarity	NPD940	Approved
0.7281	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD1470	Approved
0.7265	Intermediate Similarity	NPD2342	Discontinued
0.725	Intermediate Similarity	NPD7635	Approved
0.7222	Intermediate Similarity	NPD3092	Approved
0.7222	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD2228	Approved
0.719	Intermediate Similarity	NPD2234	Approved
0.719	Intermediate Similarity	NPD2229	Approved
0.7188	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3091	Approved
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1809	Phase 2
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.7143	Intermediate Similarity	NPD825	Approved
0.7143	Intermediate Similarity	NPD826	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD1511	Approved
0.7133	Intermediate Similarity	NPD3455	Phase 2
0.7132	Intermediate Similarity	NPD3094	Phase 2
0.712	Intermediate Similarity	NPD4093	Discontinued
0.712	Intermediate Similarity	NPD9268	Approved
0.7119	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD845	Approved
0.7109	Intermediate Similarity	NPD9622	Approved
0.7109	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD230	Phase 1
0.7068	Intermediate Similarity	NPD259	Phase 1
0.7063	Intermediate Similarity	NPD4059	Approved
0.7063	Intermediate Similarity	NPD2286	Discontinued
0.7063	Intermediate Similarity	NPD4626	Approved
0.7045	Intermediate Similarity	NPD7095	Approved
0.7045	Intermediate Similarity	NPD9536	Phase 1
0.7045	Intermediate Similarity	NPD9537	Phase 1
0.7042	Intermediate Similarity	NPD1512	Approved
0.7034	Intermediate Similarity	NPD1444	Approved
0.7034	Intermediate Similarity	NPD1445	Approved
0.7015	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1558	Phase 1
0.7015	Intermediate Similarity	NPD3620	Phase 2
0.7008	Intermediate Similarity	NPD3023	Approved
0.7008	Intermediate Similarity	NPD3026	Approved
0.7007	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1164	Approved
0.6992	Remote Similarity	NPD3764	Approved
0.6984	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3025	Approved
0.6984	Remote Similarity	NPD3024	Approved
0.6975	Remote Similarity	NPD1358	Approved
0.6972	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5535	Approved
0.6963	Remote Similarity	NPD275	Approved
0.6963	Remote Similarity	NPD274	Approved
0.6963	Remote Similarity	NPD555	Phase 2
0.6959	Remote Similarity	NPD3882	Suspended
0.6957	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9621	Approved
0.6947	Remote Similarity	NPD9619	Approved
0.6947	Remote Similarity	NPD9620	Approved
0.694	Remote Similarity	NPD2674	Phase 3
0.6939	Remote Similarity	NPD2801	Approved
0.6939	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6671	Approved
0.6929	Remote Similarity	NPD3095	Discontinued
0.6917	Remote Similarity	NPD2684	Approved
0.6901	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5736	Approved
0.6891	Remote Similarity	NPD3134	Approved
0.6891	Remote Similarity	NPD968	Approved
0.6884	Remote Similarity	NPD5405	Approved
0.6884	Remote Similarity	NPD5406	Approved
0.6884	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5408	Approved
0.6884	Remote Similarity	NPD5404	Approved
0.6875	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD3847	Discontinued
0.6871	Remote Similarity	NPD1934	Approved
0.6866	Remote Similarity	NPD597	Approved
0.6866	Remote Similarity	NPD598	Approved
0.6866	Remote Similarity	NPD601	Approved
0.6864	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD1237	Approved
0.6864	Remote Similarity	NPD9610	Approved
0.685	Remote Similarity	NPD1357	Approved
0.685	Remote Similarity	NPD1651	Approved
0.6846	Remote Similarity	NPD2983	Phase 2
0.6846	Remote Similarity	NPD2982	Phase 2
0.6829	Remote Similarity	NPD7843	Approved
0.6822	Remote Similarity	NPD1535	Discovery
0.6818	Remote Similarity	NPD6584	Phase 3
0.6818	Remote Similarity	NPD9094	Approved
0.6815	Remote Similarity	NPD1132	Approved
0.6815	Remote Similarity	NPD1130	Approved
0.6815	Remote Similarity	NPD1136	Approved
0.6812	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7157	Approved
0.6797	Remote Similarity	NPD1751	Approved
0.6797	Remote Similarity	NPD4589	Approved
0.6797	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD817	Approved
0.6788	Remote Similarity	NPD823	Approved
0.6783	Remote Similarity	NPD4357	Discontinued
0.6777	Remote Similarity	NPD74	Approved
0.6777	Remote Similarity	NPD9266	Approved
0.6774	Remote Similarity	NPD1241	Discontinued
0.6774	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5303	Approved
0.6772	Remote Similarity	NPD9545	Approved
0.6772	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5304	Approved
0.6769	Remote Similarity	NPD1481	Phase 2
0.6769	Remote Similarity	NPD3972	Approved
0.6769	Remote Similarity	NPD2981	Phase 2
0.6767	Remote Similarity	NPD3018	Phase 2
0.6767	Remote Similarity	NPD2861	Phase 2
0.6763	Remote Similarity	NPD9570	Approved
0.6748	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3144	Approved
0.6741	Remote Similarity	NPD3145	Approved
0.6738	Remote Similarity	NPD3060	Approved
0.6733	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5451	Approved
0.6719	Remote Similarity	NPD5691	Approved
0.6718	Remote Similarity	NPD1755	Approved
0.6715	Remote Similarity	NPD4340	Discontinued
0.6713	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3300	Phase 2
0.6713	Remote Similarity	NPD3845	Phase 1
0.6712	Remote Similarity	NPD1653	Approved
0.6694	Remote Similarity	NPD9264	Approved
0.6694	Remote Similarity	NPD9267	Approved
0.6694	Remote Similarity	NPD9263	Approved
0.6692	Remote Similarity	NPD2798	Approved
0.6692	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD422	Phase 1
0.6692	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2799	Discontinued
0.6691	Remote Similarity	NPD1510	Phase 2
0.6691	Remote Similarity	NPD6663	Approved
0.669	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD2420	Approved
0.6667	Remote Similarity	NPD2421	Approved
0.6667	Remote Similarity	NPD5846	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