NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.15
Volume:	307.766
LogP:	3.636
LogD:	3.655
LogS:	-4.679
# Rotatable Bonds:	6
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	2.457
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.743
MDCK Permeability:	1.292975775868399e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.188
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.741
Plasma Protein Binding (PPB):	97.6043930053711%
Volume Distribution (VD):	0.479
Pgp-substrate:	1.0203877687454224%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.742
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	4.978
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.547
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.787
Skin Sensitization:	0.904
Carcinogencity:	0.5
Eye Corrosion:	0.037
Eye Irritation:	0.985
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC283012

Natural Product ID:	NPC283012
*Common Name:**	(R)-1,7-Diphenylhepta-4,6-Dien-3-Ol
IUPAC Name:	(3R,4E,6E)-1,7-diphenylhepta-4,6-dien-3-ol
Synonyms:
Standard InCHIKey:	OVURIZIJDDTXJS-MPDYCGONSA-N
Standard InCHI:	InChI=1S/C19H20O/c20-19(16-15-18-11-5-2-6-12-18)14-8-7-13-17-9-3-1-4-10-17/h1-14,19-20H,15-16H2/b13-7+,14-8+/t19-/m0/s1
SMILES:	O[C@H](CCc1ccccc1)/C=C/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461083
PubChem CID:	44560847
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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO22901	Curcuma comosa	Species	Zingiberaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	62.51	%	PMID[470212]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	75.42	%	PMID[470212]

☑ 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 NPC283012 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	189
0.1-0.2	1246
0.2-0.3	4286
0.3-0.4	14302
0.4-0.5	14514
0.5-0.6	6367
0.6-0.7	1494
0.7-0.8	258
0.8-0.85	24
0.85-0.9	10
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475199
0.962	High Similarity	NPC99482
0.9481	High Similarity	NPC164449
0.9481	High Similarity	NPC184030
0.9241	High Similarity	NPC121478
0.9241	High Similarity	NPC73637
0.8875	High Similarity	NPC117180
0.878	High Similarity	NPC304538
0.8765	High Similarity	NPC103326
0.8765	High Similarity	NPC329319
0.8765	High Similarity	NPC87299
0.8765	High Similarity	NPC99394
0.8684	High Similarity	NPC208302
0.8636	High Similarity	NPC206764
0.8462	Intermediate Similarity	NPC108218
0.8444	Intermediate Similarity	NPC289201
0.8395	Intermediate Similarity	NPC469894
0.8375	Intermediate Similarity	NPC66655
0.8295	Intermediate Similarity	NPC187725
0.8295	Intermediate Similarity	NPC141607
0.8289	Intermediate Similarity	NPC82770
0.8289	Intermediate Similarity	NPC78954
0.8289	Intermediate Similarity	NPC239931
0.8276	Intermediate Similarity	NPC199567
0.8261	Intermediate Similarity	NPC132078
0.8261	Intermediate Similarity	NPC51333
0.8261	Intermediate Similarity	NPC78119
0.8261	Intermediate Similarity	NPC216468
0.8214	Intermediate Similarity	NPC172984
0.8172	Intermediate Similarity	NPC213730
0.8172	Intermediate Similarity	NPC294741
0.8132	Intermediate Similarity	NPC21959
0.8085	Intermediate Similarity	NPC7686
0.8085	Intermediate Similarity	NPC91461
0.8085	Intermediate Similarity	NPC40258
0.8068	Intermediate Similarity	NPC1793
0.8049	Intermediate Similarity	NPC224544
0.8046	Intermediate Similarity	NPC211237
0.8023	Intermediate Similarity	NPC475710
0.8	Intermediate Similarity	NPC128645
0.7976	Intermediate Similarity	NPC133050
0.7931	Intermediate Similarity	NPC93843
0.7907	Intermediate Similarity	NPC95429
0.7901	Intermediate Similarity	NPC189371
0.7835	Intermediate Similarity	NPC233396
0.7835	Intermediate Similarity	NPC154899
0.7826	Intermediate Similarity	NPC151715
0.7826	Intermediate Similarity	NPC76938
0.7816	Intermediate Similarity	NPC474354
0.7791	Intermediate Similarity	NPC477770
0.7766	Intermediate Similarity	NPC329387
0.7766	Intermediate Similarity	NPC317280
0.7765	Intermediate Similarity	NPC165212
0.7755	Intermediate Similarity	NPC92623
0.7755	Intermediate Similarity	NPC135464
0.7742	Intermediate Similarity	NPC32714
0.7742	Intermediate Similarity	NPC26244
0.7732	Intermediate Similarity	NPC323810
0.7727	Intermediate Similarity	NPC474211
0.7717	Intermediate Similarity	NPC325292
0.7717	Intermediate Similarity	NPC138117
0.7701	Intermediate Similarity	NPC168855
0.7692	Intermediate Similarity	NPC300017
0.7692	Intermediate Similarity	NPC220596
0.7692	Intermediate Similarity	NPC79917
0.7667	Intermediate Similarity	NPC231591
0.766	Intermediate Similarity	NPC473388
0.766	Intermediate Similarity	NPC324602
0.7653	Intermediate Similarity	NPC243601
0.7634	Intermediate Similarity	NPC20142
0.7634	Intermediate Similarity	NPC215351
0.7632	Intermediate Similarity	NPC22786
0.7629	Intermediate Similarity	NPC19856
0.7614	Intermediate Similarity	NPC123476
0.7609	Intermediate Similarity	NPC314690
0.7609	Intermediate Similarity	NPC45040
0.7604	Intermediate Similarity	NPC469481
0.76	Intermediate Similarity	NPC262365
0.7582	Intermediate Similarity	NPC280347
0.7582	Intermediate Similarity	NPC213156
0.7582	Intermediate Similarity	NPC240108
0.7582	Intermediate Similarity	NPC177420
0.7579	Intermediate Similarity	NPC474073
0.7553	Intermediate Similarity	NPC313650
0.7551	Intermediate Similarity	NPC249067
0.7528	Intermediate Similarity	NPC243166
0.7527	Intermediate Similarity	NPC271440
0.7525	Intermediate Similarity	NPC62258
0.7525	Intermediate Similarity	NPC55617
0.7525	Intermediate Similarity	NPC292758
0.7525	Intermediate Similarity	NPC65855
0.75	Intermediate Similarity	NPC472980
0.75	Intermediate Similarity	NPC27252
0.75	Intermediate Similarity	NPC472979
0.75	Intermediate Similarity	NPC192
0.75	Intermediate Similarity	NPC55561
0.7475	Intermediate Similarity	NPC211551
0.7474	Intermediate Similarity	NPC132271
0.7474	Intermediate Similarity	NPC292730
0.7474	Intermediate Similarity	NPC216520
0.7474	Intermediate Similarity	NPC82664
0.7473	Intermediate Similarity	NPC113460
0.7473	Intermediate Similarity	NPC104216
0.7473	Intermediate Similarity	NPC25493
0.7451	Intermediate Similarity	NPC174096
0.7451	Intermediate Similarity	NPC147634
0.7451	Intermediate Similarity	NPC321252
0.7451	Intermediate Similarity	NPC475018
0.7451	Intermediate Similarity	NPC252544
0.7451	Intermediate Similarity	NPC44732
0.7451	Intermediate Similarity	NPC226401
0.7451	Intermediate Similarity	NPC120982
0.7451	Intermediate Similarity	NPC79793
0.7451	Intermediate Similarity	NPC63345
0.7447	Intermediate Similarity	NPC128062
0.7444	Intermediate Similarity	NPC155393
0.7442	Intermediate Similarity	NPC309279
0.7442	Intermediate Similarity	NPC328178
0.7426	Intermediate Similarity	NPC64642
0.7426	Intermediate Similarity	NPC472982
0.7426	Intermediate Similarity	NPC149455
0.7423	Intermediate Similarity	NPC266343
0.7423	Intermediate Similarity	NPC214200
0.7423	Intermediate Similarity	NPC228400
0.74	Intermediate Similarity	NPC477251
0.7396	Intermediate Similarity	NPC210529
0.7396	Intermediate Similarity	NPC225464
0.7396	Intermediate Similarity	NPC290515
0.7396	Intermediate Similarity	NPC160548
0.7396	Intermediate Similarity	NPC226096
0.7396	Intermediate Similarity	NPC108606
0.7396	Intermediate Similarity	NPC175852
0.7396	Intermediate Similarity	NPC164514
0.7396	Intermediate Similarity	NPC303611
0.7391	Intermediate Similarity	NPC242240
0.7391	Intermediate Similarity	NPC123273
0.7391	Intermediate Similarity	NPC318325
0.7391	Intermediate Similarity	NPC172128
0.7386	Intermediate Similarity	NPC44830
0.7379	Intermediate Similarity	NPC177576
0.7379	Intermediate Similarity	NPC308689
0.7379	Intermediate Similarity	NPC187583
0.7379	Intermediate Similarity	NPC179002
0.7379	Intermediate Similarity	NPC257430
0.7379	Intermediate Similarity	NPC234376
0.7368	Intermediate Similarity	NPC274678
0.7363	Intermediate Similarity	NPC477693
0.7363	Intermediate Similarity	NPC23167
0.7363	Intermediate Similarity	NPC407
0.7363	Intermediate Similarity	NPC477704
0.7363	Intermediate Similarity	NPC307235
0.7356	Intermediate Similarity	NPC242628
0.7353	Intermediate Similarity	NPC474272
0.7353	Intermediate Similarity	NPC265211
0.7353	Intermediate Similarity	NPC306045
0.7347	Intermediate Similarity	NPC51015
0.734	Intermediate Similarity	NPC3358
0.734	Intermediate Similarity	NPC147284
0.734	Intermediate Similarity	NPC94139
0.734	Intermediate Similarity	NPC162314
0.734	Intermediate Similarity	NPC210497
0.734	Intermediate Similarity	NPC306884
0.7333	Intermediate Similarity	NPC203076
0.7333	Intermediate Similarity	NPC175313
0.732	Intermediate Similarity	NPC92730
0.732	Intermediate Similarity	NPC128723
0.7312	Intermediate Similarity	NPC47950
0.7312	Intermediate Similarity	NPC300478
0.7312	Intermediate Similarity	NPC312304
0.7312	Intermediate Similarity	NPC317645
0.7308	Intermediate Similarity	NPC290353
0.7308	Intermediate Similarity	NPC265002
0.7308	Intermediate Similarity	NPC42911
0.7308	Intermediate Similarity	NPC153795
0.73	Intermediate Similarity	NPC471133
0.73	Intermediate Similarity	NPC321670
0.7294	Intermediate Similarity	NPC9796
0.7292	Intermediate Similarity	NPC33168
0.7283	Intermediate Similarity	NPC9822
0.7283	Intermediate Similarity	NPC27974
0.7273	Intermediate Similarity	NPC168829
0.7273	Intermediate Similarity	NPC246588
0.7263	Intermediate Similarity	NPC58674
0.7255	Intermediate Similarity	NPC475282
0.7253	Intermediate Similarity	NPC194326
0.7253	Intermediate Similarity	NPC197783
0.7245	Intermediate Similarity	NPC158623
0.7245	Intermediate Similarity	NPC316797
0.7241	Intermediate Similarity	NPC127343
0.7241	Intermediate Similarity	NPC192623
0.7237	Intermediate Similarity	NPC36357
0.7237	Intermediate Similarity	NPC114327
0.7234	Intermediate Similarity	NPC265521
0.7228	Intermediate Similarity	NPC136962
0.7228	Intermediate Similarity	NPC113457
0.7222	Intermediate Similarity	NPC265146
0.7216	Intermediate Similarity	NPC32674
0.7216	Intermediate Similarity	NPC475954
0.7216	Intermediate Similarity	NPC201967
0.7216	Intermediate Similarity	NPC156313

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 NPC283012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	919
0.2-0.3	1398
0.3-0.4	3215
0.4-0.5	2068
0.5-0.6	1057
0.6-0.7	249
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD9294	Approved
0.8	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2933	Approved
0.7826	Intermediate Similarity	NPD2934	Approved
0.7742	Intermediate Similarity	NPD2859	Approved
0.7742	Intermediate Similarity	NPD2860	Approved
0.7677	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5048	Discontinued
0.7551	Intermediate Similarity	NPD1237	Approved
0.7526	Intermediate Similarity	NPD4719	Phase 2
0.75	Intermediate Similarity	NPD3020	Approved
0.7451	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6647	Phase 2
0.7396	Intermediate Similarity	NPD9609	Approved
0.7396	Intermediate Similarity	NPD9611	Approved
0.7396	Intermediate Similarity	NPD9495	Approved
0.7396	Intermediate Similarity	NPD9612	Approved
0.7386	Intermediate Similarity	NPD3971	Phase 1
0.7347	Intermediate Similarity	NPD854	Approved
0.7347	Intermediate Similarity	NPD855	Approved
0.7273	Intermediate Similarity	NPD4656	Approved
0.7273	Intermediate Similarity	NPD4658	Approved
0.7245	Intermediate Similarity	NPD2555	Approved
0.7245	Intermediate Similarity	NPD2552	Approved
0.7245	Intermediate Similarity	NPD2553	Approved
0.7245	Intermediate Similarity	NPD2550	Approved
0.7245	Intermediate Similarity	NPD2549	Approved
0.7245	Intermediate Similarity	NPD2558	Approved
0.7238	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4817	Approved
0.7172	Intermediate Similarity	NPD4189	Approved
0.7172	Intermediate Similarity	NPD4188	Approved
0.7172	Intermediate Similarity	NPD4818	Approved
0.7159	Intermediate Similarity	NPD226	Approved
0.7158	Intermediate Similarity	NPD3718	Approved
0.7158	Intermediate Similarity	NPD845	Approved
0.7158	Intermediate Similarity	NPD3719	Approved
0.7157	Intermediate Similarity	NPD6406	Approved
0.71	Intermediate Similarity	NPD3682	Approved
0.71	Intermediate Similarity	NPD3680	Approved
0.71	Intermediate Similarity	NPD4229	Approved
0.71	Intermediate Similarity	NPD4231	Approved
0.7089	Intermediate Similarity	NPD675	Discontinued
0.7083	Intermediate Similarity	NPD4814	Discontinued
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1616	Discontinued
0.7065	Intermediate Similarity	NPD4793	Discontinued
0.7059	Intermediate Similarity	NPD9716	Approved
0.7037	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD111	Approved
0.703	Intermediate Similarity	NPD309	Approved
0.703	Intermediate Similarity	NPD311	Approved
0.703	Intermediate Similarity	NPD10	Approved
0.703	Intermediate Similarity	NPD3046	Approved
0.703	Intermediate Similarity	NPD315	Approved
0.703	Intermediate Similarity	NPD3048	Approved
0.703	Intermediate Similarity	NPD3047	Approved
0.703	Intermediate Similarity	NPD5909	Discontinued
0.703	Intermediate Similarity	NPD314	Approved
0.703	Intermediate Similarity	NPD310	Approved
0.701	Intermediate Similarity	NPD844	Approved
0.701	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2629	Approved
0.7	Intermediate Similarity	NPD9491	Approved
0.6979	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7798	Approved
0.6966	Remote Similarity	NPD9250	Approved
0.6947	Remote Similarity	NPD1239	Approved
0.6931	Remote Similarity	NPD3681	Approved
0.6931	Remote Similarity	NPD5765	Approved
0.6931	Remote Similarity	NPD3683	Approved
0.6915	Remote Similarity	NPD5347	Phase 2
0.6915	Remote Similarity	NPD5346	Phase 2
0.6907	Remote Similarity	NPD3772	Phase 3
0.69	Remote Similarity	NPD3028	Approved
0.6893	Remote Similarity	NPD3524	Approved
0.6893	Remote Similarity	NPD3526	Approved
0.6893	Remote Similarity	NPD968	Approved
0.6893	Remote Similarity	NPD2559	Approved
0.6893	Remote Similarity	NPD2551	Approved
0.6875	Remote Similarity	NPD9251	Approved
0.6869	Remote Similarity	NPD5926	Approved
0.6857	Remote Similarity	NPD3021	Approved
0.6857	Remote Similarity	NPD3022	Approved
0.6848	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1989	Approved
0.6837	Remote Similarity	NPD1809	Phase 2
0.6827	Remote Similarity	NPD9532	Phase 3
0.6827	Remote Similarity	NPD2342	Discontinued
0.6818	Remote Similarity	NPD227	Approved
0.6818	Remote Similarity	NPD225	Approved
0.6809	Remote Similarity	NPD1101	Approved
0.6809	Remote Similarity	NPD531	Approved
0.6804	Remote Similarity	NPD1066	Discontinued
0.68	Remote Similarity	NPD2066	Phase 3
0.6786	Remote Similarity	NPD7725	Approved
0.6786	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD288	Approved
0.6768	Remote Similarity	NPD1875	Phase 1
0.6757	Remote Similarity	NPD7741	Discontinued
0.6757	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3091	Approved
0.6737	Remote Similarity	NPD689	Discontinued
0.6737	Remote Similarity	NPD800	Approved
0.6735	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1242	Phase 1
0.6731	Remote Similarity	NPD6685	Approved
0.6729	Remote Similarity	NPD2499	Approved
0.6729	Remote Similarity	NPD2500	Approved
0.6702	Remote Similarity	NPD1282	Approved
0.6702	Remote Similarity	NPD9538	Approved
0.6701	Remote Similarity	NPD6690	Approved
0.6701	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1710	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1086	Approved
0.6667	Remote Similarity	NPD4119	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD940	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD1089	Approved
0.6667	Remote Similarity	NPD1932	Approved
0.6667	Remote Similarity	NPD1090	Approved
0.6667	Remote Similarity	NPD3974	Phase 2
0.6637	Remote Similarity	NPD5125	Phase 3
0.6637	Remote Similarity	NPD5126	Approved
0.6637	Remote Similarity	NPD5723	Approved
0.6636	Remote Similarity	NPD4253	Approved
0.6636	Remote Similarity	NPD4254	Approved
0.6636	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7508	Discontinued
0.6609	Remote Similarity	NPD2562	Approved
0.6609	Remote Similarity	NPD2561	Approved
0.6606	Remote Similarity	NPD6010	Discontinued
0.6604	Remote Similarity	NPD4720	Approved
0.6604	Remote Similarity	NPD4718	Approved
0.6604	Remote Similarity	NPD4717	Approved
0.6604	Remote Similarity	NPD2684	Approved
0.6602	Remote Similarity	NPD1930	Approved
0.6602	Remote Similarity	NPD1929	Approved
0.6602	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1566	Phase 3
0.66	Remote Similarity	NPD1565	Approved
0.66	Remote Similarity	NPD1564	Approved
0.66	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD942	Approved
0.6574	Remote Similarity	NPD4572	Approved
0.6574	Remote Similarity	NPD4573	Approved
0.6574	Remote Similarity	NPD4571	Approved
0.6571	Remote Similarity	NPD5705	Approved
0.6571	Remote Similarity	NPD5704	Approved
0.6571	Remote Similarity	NPD5706	Approved
0.6569	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6049	Phase 2
0.6566	Remote Similarity	NPD1693	Approved
0.6566	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD9490	Approved
0.6552	Remote Similarity	NPD5159	Phase 2
0.6552	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5157	Phase 1
0.6552	Remote Similarity	NPD4659	Approved
0.6542	Remote Similarity	NPD1792	Phase 2
0.6531	Remote Similarity	NPD752	Approved
0.6531	Remote Similarity	NPD1088	Approved
0.6522	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3092	Approved
0.6517	Remote Similarity	NPD4144	Approved
0.6517	Remote Similarity	NPD4147	Approved
0.6514	Remote Similarity	NPD2496	Approved
0.6514	Remote Similarity	NPD2497	Approved
0.6509	Remote Similarity	NPD290	Approved
0.6495	Remote Similarity	NPD9256	Approved
0.6495	Remote Similarity	NPD9258	Approved
0.6491	Remote Similarity	NPD3095	Discontinued
0.6486	Remote Similarity	NPD4198	Discontinued
0.6476	Remote Similarity	NPD5717	Approved
0.6471	Remote Similarity	NPD1238	Approved
0.6471	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2231	Phase 2
0.6466	Remote Similarity	NPD2235	Phase 2
0.6465	Remote Similarity	NPD1202	Approved
0.6465	Remote Similarity	NPD719	Approved
0.6465	Remote Similarity	NPD720	Approved
0.6465	Remote Similarity	NPD1409	Phase 3
0.6455	Remote Similarity	NPD2228	Approved
0.6455	Remote Similarity	NPD2234	Approved
0.6455	Remote Similarity	NPD2229	Approved
0.6455	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4103	Phase 2
0.6441	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4106	Approved
0.6435	Remote Similarity	NPD4136	Approved
0.6435	Remote Similarity	NPD4135	Approved
0.6429	Remote Similarity	NPD530	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