NPASS Compound

Structure

NPC122239 OpenBabel07101719132D 22 21 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 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 3.4641 -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 -1.7321 -2.0000 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 0.8660 -1.5000 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 -0.5000 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 0.0000 -2.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 2.5981 -1.5000 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 21 1 0 0 0 0 19 5 1 6 0 0 0 19 20 1 0 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.27
Volume:	364.147
LogP:	4.986
LogD:	4.288
LogS:	-4.67
# Rotatable Bonds:	11
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	3.772
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.476
MDCK Permeability:	2.4591241526650265e-05
Pgp-inhibitor:	0.724
Pgp-substrate:	0.181
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.55

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	96.95866394042969%
Volume Distribution (VD):	2.439
Pgp-substrate:	3.7367026805877686%

ADMET: Metabolism

CYP1A2-inhibitor:	0.22
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.228
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	7.379
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.663
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.225
Skin Sensitization:	0.973
Carcinogencity:	0.027
Eye Corrosion:	0.1
Eye Irritation:	0.946
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC122239

Natural Product ID:	NPC122239
*Common Name:**	(2E,6E,11S,12R)-3,7,11,15-Tetramethylhexadeca-2,6,14-Triene-1,12-Diol
IUPAC Name:	(2E,6E,11S,12R)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-1,12-diol
Synonyms:
Standard InCHIKey:	NWGKNKMSGMFQKD-SSTYKLENSA-N
Standard InCHI:	InChI=1S/C20H36O2/c1-16(2)12-13-20(22)19(5)11-7-10-17(3)8-6-9-18(4)14-15-21/h8,12,14,19-22H,6-7,9-11,13,15H2,1-5H3/b17-8+,18-14+/t19-,20+/m0/s1
SMILES:	CC(=CC[C@H]([C@@H](C)CCC/C(=C/CC/C(=C/CO)/C)/C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228072
PubChem CID:	16681369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001357] Acyclic diterpenoids

*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
NPO29090	Carpesium triste	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[17432904]
NPO29090	Carpesium triste	Species	Asteraceae	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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	42.4	ug.mL-1	PMID[575298]
NPT27	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[575298]

☑ 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 NPC122239 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	147
0.1-0.2	1679
0.2-0.3	9462
0.3-0.4	16460
0.4-0.5	8257
0.5-0.6	4961
0.6-0.7	1413
0.7-0.8	251
0.8-0.85	52
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC226848
0.8966	High Similarity	NPC475931
0.8852	High Similarity	NPC308844
0.8833	High Similarity	NPC473508
0.8814	High Similarity	NPC99487
0.8793	High Similarity	NPC155025
0.873	High Similarity	NPC305698
0.873	High Similarity	NPC224532
0.8596	High Similarity	NPC329686
0.8571	High Similarity	NPC474496
0.8571	High Similarity	NPC114651
0.8571	High Similarity	NPC73603
0.8571	High Similarity	NPC259299
0.8545	High Similarity	NPC473672
0.8545	High Similarity	NPC474495
0.85	High Similarity	NPC240506
0.85	High Similarity	NPC471081
0.8475	Intermediate Similarity	NPC181872
0.8462	Intermediate Similarity	NPC4299
0.8413	Intermediate Similarity	NPC326310
0.8413	Intermediate Similarity	NPC267027
0.8413	Intermediate Similarity	NPC311736
0.8387	Intermediate Similarity	NPC309300
0.8387	Intermediate Similarity	NPC300593
0.8364	Intermediate Similarity	NPC26960
0.8364	Intermediate Similarity	NPC182102
0.8308	Intermediate Similarity	NPC101622
0.8308	Intermediate Similarity	NPC239373
0.8308	Intermediate Similarity	NPC329989
0.8281	Intermediate Similarity	NPC163290
0.8254	Intermediate Similarity	NPC19569
0.8226	Intermediate Similarity	NPC474155
0.8226	Intermediate Similarity	NPC279200
0.8226	Intermediate Similarity	NPC473759
0.8197	Intermediate Similarity	NPC66020
0.8182	Intermediate Similarity	NPC34834
0.8125	Intermediate Similarity	NPC202017
0.8125	Intermediate Similarity	NPC272125
0.8095	Intermediate Similarity	NPC290367
0.8065	Intermediate Similarity	NPC225342
0.8065	Intermediate Similarity	NPC274704
0.8065	Intermediate Similarity	NPC207007
0.8065	Intermediate Similarity	NPC475251
0.8065	Intermediate Similarity	NPC321867
0.8065	Intermediate Similarity	NPC68679
0.806	Intermediate Similarity	NPC472254
0.806	Intermediate Similarity	NPC471662
0.803	Intermediate Similarity	NPC217570
0.803	Intermediate Similarity	NPC471560
0.803	Intermediate Similarity	NPC74722
0.803	Intermediate Similarity	NPC90115
0.803	Intermediate Similarity	NPC304690
0.8	Intermediate Similarity	NPC477791
0.8	Intermediate Similarity	NPC52012
0.8	Intermediate Similarity	NPC472255
0.8	Intermediate Similarity	NPC472253
0.8	Intermediate Similarity	NPC82337
0.8	Intermediate Similarity	NPC69649
0.8	Intermediate Similarity	NPC68703
0.7966	Intermediate Similarity	NPC148216
0.7966	Intermediate Similarity	NPC148163
0.7966	Intermediate Similarity	NPC232247
0.7966	Intermediate Similarity	NPC251666
0.7966	Intermediate Similarity	NPC227135
0.7966	Intermediate Similarity	NPC281590
0.7966	Intermediate Similarity	NPC130209
0.7941	Intermediate Similarity	NPC329763
0.7941	Intermediate Similarity	NPC477085
0.7879	Intermediate Similarity	NPC167527
0.7869	Intermediate Similarity	NPC475830
0.7857	Intermediate Similarity	NPC256720
0.7857	Intermediate Similarity	NPC236228
0.7833	Intermediate Similarity	NPC48891
0.7833	Intermediate Similarity	NPC473865
0.7833	Intermediate Similarity	NPC474643
0.7833	Intermediate Similarity	NPC24443
0.7826	Intermediate Similarity	NPC306727
0.7826	Intermediate Similarity	NPC471525
0.7812	Intermediate Similarity	NPC225415
0.7812	Intermediate Similarity	NPC110241
0.7812	Intermediate Similarity	NPC96793
0.7812	Intermediate Similarity	NPC323424
0.7797	Intermediate Similarity	NPC49059
0.7797	Intermediate Similarity	NPC256209
0.7794	Intermediate Similarity	NPC477087
0.7794	Intermediate Similarity	NPC477792
0.7794	Intermediate Similarity	NPC477086
0.7778	Intermediate Similarity	NPC210346
0.7761	Intermediate Similarity	NPC473893
0.7759	Intermediate Similarity	NPC35756
0.7746	Intermediate Similarity	NPC84360
0.7746	Intermediate Similarity	NPC91594
0.7727	Intermediate Similarity	NPC136813
0.7719	Intermediate Similarity	NPC329773
0.7719	Intermediate Similarity	NPC474460
0.7714	Intermediate Similarity	NPC313179
0.7714	Intermediate Similarity	NPC69383
0.7714	Intermediate Similarity	NPC171148
0.7714	Intermediate Similarity	NPC474885
0.7692	Intermediate Similarity	NPC238352
0.7692	Intermediate Similarity	NPC477009
0.7681	Intermediate Similarity	NPC220939
0.7681	Intermediate Similarity	NPC265485
0.7681	Intermediate Similarity	NPC130665
0.7667	Intermediate Similarity	NPC223604
0.7667	Intermediate Similarity	NPC474644
0.7667	Intermediate Similarity	NPC477726
0.7667	Intermediate Similarity	NPC477725
0.7656	Intermediate Similarity	NPC83200
0.7647	Intermediate Similarity	NPC189745
0.7647	Intermediate Similarity	NPC129630
0.7647	Intermediate Similarity	NPC470041
0.7639	Intermediate Similarity	NPC167891
0.7639	Intermediate Similarity	NPC476314
0.7639	Intermediate Similarity	NPC83351
0.7636	Intermediate Similarity	NPC165651
0.7636	Intermediate Similarity	NPC210560
0.7636	Intermediate Similarity	NPC87439
0.7636	Intermediate Similarity	NPC140501
0.7636	Intermediate Similarity	NPC24824
0.7612	Intermediate Similarity	NPC272961
0.7612	Intermediate Similarity	NPC96484
0.7612	Intermediate Similarity	NPC208999
0.7612	Intermediate Similarity	NPC471238
0.7606	Intermediate Similarity	NPC271070
0.7606	Intermediate Similarity	NPC310643
0.7606	Intermediate Similarity	NPC265588
0.7586	Intermediate Similarity	NPC244038
0.7571	Intermediate Similarity	NPC471659
0.7571	Intermediate Similarity	NPC201048
0.7571	Intermediate Similarity	NPC476366
0.7541	Intermediate Similarity	NPC470966
0.7541	Intermediate Similarity	NPC470968
0.7541	Intermediate Similarity	NPC477661
0.7541	Intermediate Similarity	NPC470967
0.7541	Intermediate Similarity	NPC471960
0.7541	Intermediate Similarity	NPC475384
0.7541	Intermediate Similarity	NPC473847
0.7541	Intermediate Similarity	NPC470969
0.7541	Intermediate Similarity	NPC161838
0.7536	Intermediate Similarity	NPC242001
0.7536	Intermediate Similarity	NPC23954
0.7534	Intermediate Similarity	NPC84694
0.7534	Intermediate Similarity	NPC109546
0.7534	Intermediate Similarity	NPC28862
0.7534	Intermediate Similarity	NPC47982
0.7534	Intermediate Similarity	NPC81306
0.7534	Intermediate Similarity	NPC143182
0.75	Intermediate Similarity	NPC474248
0.75	Intermediate Similarity	NPC477426
0.75	Intermediate Similarity	NPC476703
0.75	Intermediate Similarity	NPC40049
0.75	Intermediate Similarity	NPC470711
0.75	Intermediate Similarity	NPC477425
0.75	Intermediate Similarity	NPC476007
0.75	Intermediate Similarity	NPC477427
0.75	Intermediate Similarity	NPC470758
0.75	Intermediate Similarity	NPC471061
0.75	Intermediate Similarity	NPC474826
0.7465	Intermediate Similarity	NPC23231
0.7465	Intermediate Similarity	NPC32832
0.7465	Intermediate Similarity	NPC60818
0.7463	Intermediate Similarity	NPC278895
0.7463	Intermediate Similarity	NPC96962
0.746	Intermediate Similarity	NPC278202
0.7432	Intermediate Similarity	NPC96362
0.7432	Intermediate Similarity	NPC234193
0.7429	Intermediate Similarity	NPC275098
0.7429	Intermediate Similarity	NPC471799
0.7429	Intermediate Similarity	NPC234527
0.7429	Intermediate Similarity	NPC14352
0.7424	Intermediate Similarity	NPC61503
0.7424	Intermediate Similarity	NPC471200
0.7424	Intermediate Similarity	NPC287339
0.7419	Intermediate Similarity	NPC11130
0.7419	Intermediate Similarity	NPC470970
0.7414	Intermediate Similarity	NPC131623
0.7397	Intermediate Similarity	NPC474216
0.7397	Intermediate Similarity	NPC475994
0.7391	Intermediate Similarity	NPC145498
0.7391	Intermediate Similarity	NPC286154
0.7391	Intermediate Similarity	NPC329904
0.7391	Intermediate Similarity	NPC473361
0.7385	Intermediate Similarity	NPC211291
0.7385	Intermediate Similarity	NPC474480
0.7385	Intermediate Similarity	NPC133368
0.7377	Intermediate Similarity	NPC67508
0.7377	Intermediate Similarity	NPC473735
0.7377	Intermediate Similarity	NPC473721
0.7377	Intermediate Similarity	NPC473896
0.7377	Intermediate Similarity	NPC473725
0.7377	Intermediate Similarity	NPC475353
0.7377	Intermediate Similarity	NPC84824
0.7377	Intermediate Similarity	NPC473910
0.7361	Intermediate Similarity	NPC253190
0.7361	Intermediate Similarity	NPC469880
0.7361	Intermediate Similarity	NPC170148
0.7361	Intermediate Similarity	NPC470749
0.7361	Intermediate Similarity	NPC279537
0.7361	Intermediate Similarity	NPC247325

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 NPC122239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	2276
0.2-0.3	4053
0.3-0.4	1944
0.4-0.5	547
0.5-0.6	113
0.6-0.7	66
0.7-0.8	4
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8065	Intermediate Similarity	NPD368	Approved
0.7966	Intermediate Similarity	NPD342	Phase 1
0.7714	Intermediate Similarity	NPD8264	Approved
0.7636	Intermediate Similarity	NPD4265	Approved
0.7397	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6924	Approved
0.7324	Intermediate Similarity	NPD6926	Approved
0.7297	Intermediate Similarity	NPD6929	Approved
0.726	Intermediate Similarity	NPD6925	Approved
0.726	Intermediate Similarity	NPD5776	Phase 2
0.7246	Intermediate Similarity	NPD6922	Approved
0.7246	Intermediate Similarity	NPD6923	Approved
0.72	Intermediate Similarity	NPD6931	Approved
0.72	Intermediate Similarity	NPD7514	Phase 3
0.72	Intermediate Similarity	NPD4822	Approved
0.72	Intermediate Similarity	NPD4820	Approved
0.72	Intermediate Similarity	NPD7332	Phase 2
0.72	Intermediate Similarity	NPD6930	Phase 2
0.72	Intermediate Similarity	NPD4819	Approved
0.72	Intermediate Similarity	NPD4821	Approved
0.7162	Intermediate Similarity	NPD7145	Approved
0.7162	Intermediate Similarity	NPD4271	Approved
0.7162	Intermediate Similarity	NPD4268	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD5332	Approved
0.7143	Intermediate Similarity	NPD5331	Approved
0.7143	Intermediate Similarity	NPD7154	Phase 3
0.7143	Intermediate Similarity	NPD7143	Approved
0.7143	Intermediate Similarity	NPD7144	Approved
0.7123	Intermediate Similarity	NPD6933	Approved
0.7105	Intermediate Similarity	NPD6902	Approved
0.7105	Intermediate Similarity	NPD4790	Discontinued
0.7042	Intermediate Similarity	NPD7150	Approved
0.7042	Intermediate Similarity	NPD7152	Approved
0.7042	Intermediate Similarity	NPD7151	Approved
0.7013	Intermediate Similarity	NPD4270	Approved
0.7013	Intermediate Similarity	NPD4269	Approved
0.6986	Remote Similarity	NPD7339	Approved
0.6986	Remote Similarity	NPD6942	Approved
0.6984	Remote Similarity	NPD4219	Approved
0.6974	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4732	Discontinued
0.6933	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6695	Phase 3
0.6892	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6898	Phase 1
0.6835	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6932	Approved
0.6753	Remote Similarity	NPD4252	Approved
0.6753	Remote Similarity	NPD7509	Discontinued
0.675	Remote Similarity	NPD5363	Approved
0.675	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5786	Approved
0.6623	Remote Similarity	NPD7645	Phase 2
0.6623	Remote Similarity	NPD6683	Phase 2
0.6585	Remote Similarity	NPD7524	Approved
0.6585	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7750	Discontinued
0.6571	Remote Similarity	NPD7331	Phase 2
0.6543	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7525	Registered
0.6471	Remote Similarity	NPD7983	Approved
0.6456	Remote Similarity	NPD5369	Approved
0.642	Remote Similarity	NPD4786	Approved
0.642	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5779	Approved
0.6395	Remote Similarity	NPD5778	Approved
0.6386	Remote Similarity	NPD4250	Approved
0.6386	Remote Similarity	NPD4251	Approved
0.6377	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3667	Approved
0.6353	Remote Similarity	NPD6698	Approved
0.6353	Remote Similarity	NPD5785	Approved
0.6353	Remote Similarity	NPD7838	Discovery
0.6353	Remote Similarity	NPD46	Approved
0.6329	Remote Similarity	NPD5368	Approved
0.6286	Remote Similarity	NPD3197	Phase 1
0.6279	Remote Similarity	NPD7637	Suspended
0.6279	Remote Similarity	NPD7087	Discontinued
0.6265	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5370	Suspended
0.6197	Remote Similarity	NPD7341	Phase 2
0.6184	Remote Similarity	NPD4784	Approved
0.6184	Remote Similarity	NPD4785	Approved
0.618	Remote Similarity	NPD7839	Suspended
0.6173	Remote Similarity	NPD6435	Approved
0.6163	Remote Similarity	NPD7136	Phase 2
0.6133	Remote Similarity	NPD4243	Approved
0.6125	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6110	Phase 1
0.6092	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6101	Approved
0.6044	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD3665	Phase 1
0.6024	Remote Similarity	NPD3666	Approved
0.6024	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4191	Approved
0.5952	Remote Similarity	NPD1696	Phase 3
0.5926	Remote Similarity	NPD4748	Discontinued
0.5914	Remote Similarity	NPD5344	Discontinued
0.5909	Remote Similarity	NPD3195	Phase 2
0.5909	Remote Similarity	NPD4266	Approved
0.5909	Remote Similarity	NPD3194	Approved
0.5909	Remote Similarity	NPD6411	Approved
0.5909	Remote Similarity	NPD3196	Approved
0.5897	Remote Similarity	NPD8039	Approved
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD3618	Phase 1
0.587	Remote Similarity	NPD4225	Approved
0.5867	Remote Similarity	NPD1082	Approved
0.5867	Remote Similarity	NPD15	Approved
0.5867	Remote Similarity	NPD791	Approved
0.5862	Remote Similarity	NPD5328	Approved
0.5833	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7640	Approved
0.5806	Remote Similarity	NPD385	Approved
0.5806	Remote Similarity	NPD384	Approved
0.5806	Remote Similarity	NPD7639	Approved
0.5797	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3172	Approved
0.575	Remote Similarity	NPD4756	Discovery
0.5732	Remote Similarity	NPD4695	Discontinued
0.573	Remote Similarity	NPD7515	Phase 2
0.573	Remote Similarity	NPD6079	Approved
0.5699	Remote Similarity	NPD7638	Approved
0.5698	Remote Similarity	NPD6422	Discontinued
0.5698	Remote Similarity	NPD4623	Approved
0.5698	Remote Similarity	NPD4519	Discontinued
0.5696	Remote Similarity	NPD5275	Approved
0.5696	Remote Similarity	NPD4190	Phase 3
0.5694	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3732	Approved
0.5676	Remote Similarity	NPD3704	Approved
0.567	Remote Similarity	NPD6640	Phase 3
0.5667	Remote Similarity	NPD1462	Approved
0.5667	Remote Similarity	NPD6399	Phase 3
0.5647	Remote Similarity	NPD3668	Phase 3
0.5647	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6648	Approved
0.5634	Remote Similarity	NPD1145	Discontinued
0.5625	Remote Similarity	NPD1346	Approved
0.561	Remote Similarity	NPD4195	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