NPASS Compound

Structure

CID179726 OpenBabel06191715552D 21 22 0 0 0 0 0 0 0 0999 V2000 -8.6603 1.0000 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 -7.7942 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 1.7321 -0.0000 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 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -6.0622 -0.5000 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 -5.1962 -0.0000 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 -3.4641 -0.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -4.3301 -1.5000 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 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	276.12
Volume:	311.283
LogP:	3.348
LogD:	3.582
LogS:	-4.968
# Rotatable Bonds:	6
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	2.031
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	1.3553946700994857e-05
Pgp-inhibitor:	0.766
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.686
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.776
Plasma Protein Binding (PPB):	97.9351577758789%
Volume Distribution (VD):	0.678
Pgp-substrate:	0.4622390866279602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.555
CYP3A4-inhibitor:	0.305
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	7.446
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.562
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.966
Carcinogencity:	0.726
Eye Corrosion:	0.851
Eye Irritation:	0.991
Respiratory Toxicity:	0.581

Download Data

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

Natural Product: NPC179726

Natural Product ID:	NPC179726
*Common Name:**	(1E,6E)-1,7-Diphenylhepta-1,6-Diene-3,5-Dione
IUPAC Name:	(1E,6E)-1,7-diphenylhepta-1,6-diene-3,5-dione
Synonyms:
Standard InCHIKey:	UXLWOYFDJVFCBR-PHEQNACWSA-N
Standard InCHI:	InChI=1S/C19H16O2/c20-18(13-11-16-7-3-1-4-8-16)15-19(21)14-12-17-9-5-2-6-10-17/h1-14H,15H2/b13-11+,14-12+
SMILES:	O=C(CC(=O)/C=C/c1ccccc1)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL102914
PubChem CID:	5469422
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
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	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

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	>	300000.0	nM	PMID[555542]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	200000.0	nM	PMID[555543]

☑ 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 NPC179726 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	221
0.1-0.2	2863
0.2-0.3	7902
0.3-0.4	15293
0.4-0.5	13012
0.5-0.6	2759
0.6-0.7	460
0.7-0.8	153
0.8-0.85	20
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC151405
0.92	High Similarity	NPC139901
0.8947	High Similarity	NPC272260
0.875	High Similarity	NPC98880
0.8734	High Similarity	NPC273758
0.8684	High Similarity	NPC9796
0.863	High Similarity	NPC95289
0.8611	High Similarity	NPC311343
0.859	High Similarity	NPC71664
0.8537	High Similarity	NPC69057
0.8519	High Similarity	NPC123476
0.8481	Intermediate Similarity	NPC273033
0.8481	Intermediate Similarity	NPC12936
0.8354	Intermediate Similarity	NPC477703
0.8354	Intermediate Similarity	NPC164086
0.8354	Intermediate Similarity	NPC95868
0.8228	Intermediate Similarity	NPC300205
0.8205	Intermediate Similarity	NPC245966
0.8101	Intermediate Similarity	NPC285470
0.8101	Intermediate Similarity	NPC36342
0.8101	Intermediate Similarity	NPC2785
0.8049	Intermediate Similarity	NPC208183
0.8049	Intermediate Similarity	NPC243289
0.8026	Intermediate Similarity	NPC74458
0.8026	Intermediate Similarity	NPC326200
0.8	Intermediate Similarity	NPC477693
0.8	Intermediate Similarity	NPC169222
0.8	Intermediate Similarity	NPC235059
0.8	Intermediate Similarity	NPC16190
0.8	Intermediate Similarity	NPC477704
0.7975	Intermediate Similarity	NPC329318
0.7922	Intermediate Similarity	NPC285679
0.7917	Intermediate Similarity	NPC22786
0.7901	Intermediate Similarity	NPC17408
0.7901	Intermediate Similarity	NPC190567
0.7901	Intermediate Similarity	NPC285716
0.7882	Intermediate Similarity	NPC194326
0.7875	Intermediate Similarity	NPC137847
0.7875	Intermediate Similarity	NPC76455
0.7841	Intermediate Similarity	NPC59677
0.7831	Intermediate Similarity	NPC215008
0.7816	Intermediate Similarity	NPC19256
0.7805	Intermediate Similarity	NPC145053
0.7805	Intermediate Similarity	NPC73978
0.7791	Intermediate Similarity	NPC267262
0.7746	Intermediate Similarity	NPC36357
0.7746	Intermediate Similarity	NPC114327
0.7727	Intermediate Similarity	NPC284475
0.7722	Intermediate Similarity	NPC32203
0.7722	Intermediate Similarity	NPC206800
0.7701	Intermediate Similarity	NPC113307
0.7701	Intermediate Similarity	NPC231591
0.7701	Intermediate Similarity	NPC418308
0.7692	Intermediate Similarity	NPC289201
0.7674	Intermediate Similarity	NPC43945
0.7654	Intermediate Similarity	NPC103488
0.7647	Intermediate Similarity	NPC53299
0.764	Intermediate Similarity	NPC155232
0.764	Intermediate Similarity	NPC1682
0.764	Intermediate Similarity	NPC153885
0.764	Intermediate Similarity	NPC77273
0.764	Intermediate Similarity	NPC188844
0.7614	Intermediate Similarity	NPC303967
0.7614	Intermediate Similarity	NPC277277
0.7614	Intermediate Similarity	NPC110420
0.7614	Intermediate Similarity	NPC67585
0.7609	Intermediate Similarity	NPC49994
0.759	Intermediate Similarity	NPC71795
0.7586	Intermediate Similarity	NPC157778
0.7582	Intermediate Similarity	NPC12695
0.7564	Intermediate Similarity	NPC155429
0.7556	Intermediate Similarity	NPC238219
0.7556	Intermediate Similarity	NPC34243
0.7556	Intermediate Similarity	NPC289883
0.7534	Intermediate Similarity	NPC246588
0.7531	Intermediate Similarity	NPC3672
0.7531	Intermediate Similarity	NPC287790
0.7528	Intermediate Similarity	NPC141607
0.7528	Intermediate Similarity	NPC133461
0.7528	Intermediate Similarity	NPC187725
0.75	Intermediate Similarity	NPC278228
0.75	Intermediate Similarity	NPC240042
0.75	Intermediate Similarity	NPC239185
0.75	Intermediate Similarity	NPC103048
0.7474	Intermediate Similarity	NPC68269
0.7473	Intermediate Similarity	NPC472880
0.7473	Intermediate Similarity	NPC260233
0.7468	Intermediate Similarity	NPC271437
0.7444	Intermediate Similarity	NPC323420
0.7442	Intermediate Similarity	NPC475710
0.7439	Intermediate Similarity	NPC50192
0.7439	Intermediate Similarity	NPC176228
0.7432	Intermediate Similarity	NPC200745
0.7419	Intermediate Similarity	NPC134882
0.7419	Intermediate Similarity	NPC476120
0.7416	Intermediate Similarity	NPC213156
0.7416	Intermediate Similarity	NPC173413
0.7416	Intermediate Similarity	NPC240108
0.7416	Intermediate Similarity	NPC108026
0.7412	Intermediate Similarity	NPC308619
0.7412	Intermediate Similarity	NPC127491
0.7412	Intermediate Similarity	NPC324835
0.7412	Intermediate Similarity	NPC324624
0.7407	Intermediate Similarity	NPC78500
0.7391	Intermediate Similarity	NPC219573
0.7391	Intermediate Similarity	NPC185208
0.7381	Intermediate Similarity	NPC100039
0.7381	Intermediate Similarity	NPC303245
0.7381	Intermediate Similarity	NPC89950
0.7375	Intermediate Similarity	NPC208075
0.7356	Intermediate Similarity	NPC160339
0.7356	Intermediate Similarity	NPC307
0.7349	Intermediate Similarity	NPC167577
0.7349	Intermediate Similarity	NPC78517
0.7333	Intermediate Similarity	NPC476484
0.7333	Intermediate Similarity	NPC113670
0.7326	Intermediate Similarity	NPC44546
0.7324	Intermediate Similarity	NPC149436
0.7312	Intermediate Similarity	NPC265220
0.7303	Intermediate Similarity	NPC298115
0.7303	Intermediate Similarity	NPC325709
0.7303	Intermediate Similarity	NPC9822
0.7297	Intermediate Similarity	NPC210849
0.7294	Intermediate Similarity	NPC99240
0.7294	Intermediate Similarity	NPC73637
0.7294	Intermediate Similarity	NPC121478
0.7292	Intermediate Similarity	NPC475939
0.7292	Intermediate Similarity	NPC472691
0.7292	Intermediate Similarity	NPC474866
0.7292	Intermediate Similarity	NPC471829
0.7283	Intermediate Similarity	NPC206764
0.7263	Intermediate Similarity	NPC109514
0.7263	Intermediate Similarity	NPC472879
0.7263	Intermediate Similarity	NPC476993
0.7262	Intermediate Similarity	NPC184030
0.7262	Intermediate Similarity	NPC164449
0.7237	Intermediate Similarity	NPC291066
0.7234	Intermediate Similarity	NPC75724
0.7234	Intermediate Similarity	NPC145052
0.7234	Intermediate Similarity	NPC179411
0.7234	Intermediate Similarity	NPC201967
0.7222	Intermediate Similarity	NPC269586
0.7222	Intermediate Similarity	NPC26224
0.7222	Intermediate Similarity	NPC198841
0.7209	Intermediate Similarity	NPC39600
0.7209	Intermediate Similarity	NPC44830
0.7209	Intermediate Similarity	NPC197581
0.72	Intermediate Similarity	NPC71009
0.7174	Intermediate Similarity	NPC261181
0.7172	Intermediate Similarity	NPC470007
0.7158	Intermediate Similarity	NPC130193
0.7158	Intermediate Similarity	NPC54647
0.7143	Intermediate Similarity	NPC36440
0.7143	Intermediate Similarity	NPC475023
0.7143	Intermediate Similarity	NPC119631
0.7143	Intermediate Similarity	NPC167336
0.7143	Intermediate Similarity	NPC475059
0.7143	Intermediate Similarity	NPC103346
0.7128	Intermediate Similarity	NPC472788
0.7126	Intermediate Similarity	NPC95429
0.7123	Intermediate Similarity	NPC120441
0.7123	Intermediate Similarity	NPC65873
0.7123	Intermediate Similarity	NPC300345
0.7123	Intermediate Similarity	NPC212114
0.7113	Intermediate Similarity	NPC329556
0.7108	Intermediate Similarity	NPC298023
0.7097	Intermediate Similarity	NPC473347
0.7093	Intermediate Similarity	NPC283012
0.7093	Intermediate Similarity	NPC323103
0.7093	Intermediate Similarity	NPC475199
0.7083	Intermediate Similarity	NPC277704
0.7071	Intermediate Similarity	NPC95178
0.7071	Intermediate Similarity	NPC29989
0.7071	Intermediate Similarity	NPC472699
0.7071	Intermediate Similarity	NPC69332
0.7071	Intermediate Similarity	NPC472700
0.7065	Intermediate Similarity	NPC475057
0.7059	Intermediate Similarity	NPC127343
0.7059	Intermediate Similarity	NPC157055
0.7053	Intermediate Similarity	NPC317280
0.7053	Intermediate Similarity	NPC329387
0.7051	Intermediate Similarity	NPC267443
0.7045	Intermediate Similarity	NPC252067
0.7045	Intermediate Similarity	NPC95965
0.7045	Intermediate Similarity	NPC99482
0.703	Intermediate Similarity	NPC88141
0.7027	Intermediate Similarity	NPC8235
0.7011	Intermediate Similarity	NPC149263
0.7011	Intermediate Similarity	NPC270507
0.7	Intermediate Similarity	NPC473345
0.7	Intermediate Similarity	NPC472701
0.7	Intermediate Similarity	NPC472683
0.7	Intermediate Similarity	NPC472695
0.7	Intermediate Similarity	NPC472696
0.6988	Remote Similarity	NPC175393
0.6979	Remote Similarity	NPC476042
0.6979	Remote Similarity	NPC474308
0.6962	Remote Similarity	NPC78954
0.6962	Remote Similarity	NPC82770
0.6962	Remote Similarity	NPC239931

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 NPC179726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1211
0.2-0.3	1541
0.3-0.4	3577
0.4-0.5	1899
0.5-0.6	593
0.6-0.7	103
0.7-0.8	20
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8481	Intermediate Similarity	NPD942	Approved
0.8354	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD1508	Approved
0.7727	Intermediate Similarity	NPD7609	Phase 3
0.7722	Intermediate Similarity	NPD9716	Approved
0.7674	Intermediate Similarity	NPD650	Approved
0.764	Intermediate Similarity	NPD7631	Approved
0.7619	Intermediate Similarity	NPD3971	Phase 1
0.7582	Intermediate Similarity	NPD1843	Approved
0.75	Intermediate Similarity	NPD3495	Discontinued
0.7363	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD2066	Phase 3
0.7333	Intermediate Similarity	NPD675	Discontinued
0.7333	Intermediate Similarity	NPD1007	Discontinued
0.7273	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD225	Approved
0.7229	Intermediate Similarity	NPD227	Approved
0.7188	Intermediate Similarity	NPD1932	Approved
0.7174	Intermediate Similarity	NPD1202	Approved
0.7113	Intermediate Similarity	NPD1929	Approved
0.7113	Intermediate Similarity	NPD1930	Approved
0.7113	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4094	Approved
0.7045	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD226	Approved
0.6947	Remote Similarity	NPD4655	Approved
0.6947	Remote Similarity	NPD4657	Approved
0.6941	Remote Similarity	NPD9490	Approved
0.6889	Remote Similarity	NPD1282	Approved
0.6889	Remote Similarity	NPD4793	Discontinued
0.6875	Remote Similarity	NPD5926	Approved
0.6869	Remote Similarity	NPD1237	Approved
0.6869	Remote Similarity	NPD5909	Discontinued
0.6842	Remote Similarity	NPD1989	Approved
0.6842	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2171	Approved
0.6837	Remote Similarity	NPD2648	Phase 3
0.6837	Remote Similarity	NPD2193	Phase 2
0.6818	Remote Similarity	NPD9491	Approved
0.6804	Remote Similarity	NPD1238	Approved
0.6804	Remote Similarity	NPD7798	Approved
0.6778	Remote Similarity	NPD9259	Approved
0.6778	Remote Similarity	NPD9257	Approved
0.6774	Remote Similarity	NPD1239	Approved
0.6771	Remote Similarity	NPD1100	Approved
0.6771	Remote Similarity	NPD1099	Approved
0.6768	Remote Similarity	NPD6647	Phase 2
0.6765	Remote Similarity	NPD2329	Discontinued
0.6739	Remote Similarity	NPD5346	Phase 2
0.6739	Remote Similarity	NPD5347	Phase 2
0.6737	Remote Similarity	NPD6049	Phase 2
0.6737	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4144	Approved
0.6706	Remote Similarity	NPD4147	Approved
0.6703	Remote Similarity	NPD1087	Approved
0.67	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6024	Approved
0.6667	Remote Similarity	NPD6027	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD2196	Discontinued
0.6632	Remote Similarity	NPD1563	Approved
0.66	Remote Similarity	NPD3357	Discontinued
0.6582	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1693	Approved
0.6559	Remote Similarity	NPD800	Approved
0.6514	Remote Similarity	NPD5536	Phase 2
0.6489	Remote Similarity	NPD1089	Approved
0.6489	Remote Similarity	NPD9258	Approved
0.6489	Remote Similarity	NPD9256	Approved
0.6489	Remote Similarity	NPD1090	Approved
0.6489	Remote Similarity	NPD1086	Approved
0.6477	Remote Similarity	NPD3981	Approved
0.6477	Remote Similarity	NPD3979	Approved
0.6477	Remote Similarity	NPD3904	Approved
0.6477	Remote Similarity	NPD3903	Approved
0.6476	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2197	Approved
0.6471	Remote Similarity	NPD5048	Discontinued
0.6471	Remote Similarity	NPD2192	Approved
0.6429	Remote Similarity	NPD1566	Phase 3
0.6429	Remote Similarity	NPD1564	Approved
0.6429	Remote Similarity	NPD1565	Approved
0.6404	Remote Similarity	NPD3035	Approved
0.6404	Remote Similarity	NPD4027	Approved
0.6404	Remote Similarity	NPD4026	Approved
0.64	Remote Similarity	NPD5630	Phase 1
0.64	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2934	Approved
0.6392	Remote Similarity	NPD2933	Approved
0.6383	Remote Similarity	NPD689	Discontinued
0.6355	Remote Similarity	NPD7094	Approved
0.6355	Remote Similarity	NPD6858	Approved
0.6354	Remote Similarity	NPD1088	Approved
0.6346	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4169	Approved
0.6333	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4170	Approved
0.6327	Remote Similarity	NPD2859	Approved
0.6327	Remote Similarity	NPD2860	Approved
0.6311	Remote Similarity	NPD1677	Discontinued
0.6289	Remote Similarity	NPD1066	Discontinued
0.6286	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD1673	Approved
0.6264	Remote Similarity	NPD2001	Discontinued
0.6264	Remote Similarity	NPD4635	Approved
0.6239	Remote Similarity	NPD5951	Approved
0.6226	Remote Similarity	NPD1317	Discontinued
0.6226	Remote Similarity	NPD664	Approved
0.6224	Remote Similarity	NPD9260	Approved
0.6216	Remote Similarity	NPD7610	Discontinued
0.6211	Remote Similarity	NPD1629	Approved
0.6211	Remote Similarity	NPD1628	Approved
0.6196	Remote Similarity	NPD2539	Approved
0.6196	Remote Similarity	NPD5178	Approved
0.6196	Remote Similarity	NPD2538	Approved
0.6196	Remote Similarity	NPD4544	Approved
0.6196	Remote Similarity	NPD3429	Approved
0.6196	Remote Similarity	NPD3427	Approved
0.6195	Remote Similarity	NPD5836	Discontinued
0.618	Remote Similarity	NPD1475	Approved
0.6176	Remote Similarity	NPD813	Approved
0.6174	Remote Similarity	NPD3972	Approved
0.6168	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7009	Phase 2
0.6147	Remote Similarity	NPD7076	Approved
0.6147	Remote Similarity	NPD7077	Approved
0.6146	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4879	Approved
0.6139	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3020	Approved
0.6136	Remote Similarity	NPD9294	Approved
0.6132	Remote Similarity	NPD2182	Approved
0.6129	Remote Similarity	NPD5916	Discontinued
0.6121	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD294	Approved
0.6118	Remote Similarity	NPD292	Approved
0.6117	Remote Similarity	NPD5765	Approved
0.6117	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1617	Discontinued
0.61	Remote Similarity	NPD1875	Phase 1
0.6095	Remote Similarity	NPD5704	Approved
0.6095	Remote Similarity	NPD3134	Approved
0.6095	Remote Similarity	NPD5706	Approved
0.6095	Remote Similarity	NPD5705	Approved
0.6087	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6287	Discontinued
0.6087	Remote Similarity	NPD423	Phase 3
0.6078	Remote Similarity	NPD3028	Approved
0.6075	Remote Similarity	NPD5239	Approved
0.6075	Remote Similarity	NPD2067	Discontinued
0.6075	Remote Similarity	NPD5235	Approved
0.6075	Remote Similarity	NPD5237	Approved
0.6075	Remote Similarity	NPD5240	Approved
0.6075	Remote Similarity	NPD5236	Approved
0.6064	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4636	Approved
0.6064	Remote Similarity	NPD4406	Approved
0.6064	Remote Similarity	NPD4409	Approved
0.6058	Remote Similarity	NPD164	Approved
0.6053	Remote Similarity	NPD2345	Approved
0.6047	Remote Similarity	NPD9728	Phase 1
0.604	Remote Similarity	NPD9495	Approved
0.6034	Remote Similarity	NPD4878	Approved
0.6019	Remote Similarity	NPD4803	Discontinued
0.6019	Remote Similarity	NPD5927	Discontinued
0.6	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3428	Approved
0.6	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4146	Approved
0.6	Remote Similarity	NPD3426	Approved
0.6	Remote Similarity	NPD2895	Discontinued
0.6	Remote Similarity	NPD1241	Discontinued
0.6	Remote Similarity	NPD4145	Approved
0.6	Remote Similarity	NPD2002	Discontinued
0.5983	Remote Similarity	NPD5157	Phase 1
0.5983	Remote Similarity	NPD5159	Phase 2
0.5983	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD9591	Approved
0.5977	Remote Similarity	NPD9592	Approved
0.5977	Remote Similarity	NPD9589	Approved
0.5977	Remote Similarity	NPD9588	Approved
0.5977	Remote Similarity	NPD505	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD9590	Approved
0.5977	Remote Similarity	NPD9593	Approved
0.5977	Remote Similarity	NPD9594	Approved
0.5977	Remote Similarity	NPD80	Approved
0.5962	Remote Similarity	NPD9261	Approved
0.5955	Remote Similarity	NPD603	Approved
0.5946	Remote Similarity	NPD3867	Phase 2
0.5946	Remote Similarity	NPD1246	Approved
0.5943	Remote Similarity	NPD7130	Phase 3
0.5943	Remote Similarity	NPD6685	Approved
0.5941	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD9566	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