NPASS Compound

Structure

CID294741 OpenBabel06191716102D 24 25 0 0 1 0 0 0 0 0999 V2000 5.1962 2.0000 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 6.0622 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 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -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 -0.8660 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 -0.0000 2.0000 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 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 1 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 10.3923 2.0000 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 1 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 10 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 15 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 19 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.22
Volume:	373.717
LogP:	5.959
LogD:	4.349
LogS:	-3.96
# Rotatable Bonds:	11
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	2.331
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	1.433213947166223e-05
Pgp-inhibitor:	0.626
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	97.85950469970703%
Volume Distribution (VD):	1.161
Pgp-substrate:	0.5926734209060669%

ADMET: Metabolism

CYP1A2-inhibitor:	0.895
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.856
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.767
CYP2D6-substrate:	0.32
CYP3A4-inhibitor:	0.538
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	9.154
Half-life (T1/2):	0.365

ADMET: Toxicity

hERG Blockers:	0.243
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.949
Carcinogencity:	0.041
Eye Corrosion:	0.551
Eye Irritation:	0.979
Respiratory Toxicity:	0.336

Download Data

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

Natural Product: NPC294741

Natural Product ID:	NPC294741
*Common Name:**	Kneglomeratanol
IUPAC Name:	3-[(10S)-10-hydroxy-10-phenyldecyl]phenol
Synonyms:	Kneglomeratanol
Standard InCHIKey:	MFDBSKOHHOKJHW-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C22H30O2/c23-21-16-11-13-19(18-21)12-7-4-2-1-3-5-10-17-22(24)20-14-8-6-9-15-20/h6,8-9,11,13-16,18,22-24H,1-5,7,10,12,17H2/t22-/m0/s1
SMILES:	C(CCCCc1cccc(c1)O)CCCC[C@@H](c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513977
PubChem CID:	11723929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO11253	Knema glomerata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201311]
NPO5999	Schinopsis balansae	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7853	Baphia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11253	Knema glomerata	Species	Myristicaceae	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
ED50	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.99	ug ml-1	PMID[496252]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.32	ug ml-1	PMID[496252]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	9.33	ug ml-1	PMID[496252]
NPT140	Organism	Artemia	Artemia	LC50	=	0.21	ug.mL-1	PMID[496252]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	29.0	%	PMID[496252]

☑ 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 NPC294741 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	238
0.1-0.2	1326
0.2-0.3	4051
0.3-0.4	12870
0.4-0.5	7056
0.5-0.6	9918
0.6-0.7	5346
0.7-0.8	1509
0.8-0.85	282
0.85-0.9	77
0.9-0.95	23
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC323810
0.9474	High Similarity	NPC51333
0.9474	High Similarity	NPC132078
0.9474	High Similarity	NPC216468
0.9474	High Similarity	NPC78119
0.9462	High Similarity	NPC76938
0.9375	High Similarity	NPC213730
0.9368	High Similarity	NPC474073
0.9362	High Similarity	NPC32714
0.9278	High Similarity	NPC91461
0.9278	High Similarity	NPC7686
0.9278	High Similarity	NPC40258
0.9208	High Similarity	NPC62258
0.9208	High Similarity	NPC55617
0.9158	High Similarity	NPC274678
0.914	High Similarity	NPC192
0.9118	High Similarity	NPC174096
0.9118	High Similarity	NPC226401
0.9118	High Similarity	NPC120982
0.9118	High Similarity	NPC147634
0.9118	High Similarity	NPC79793
0.9053	High Similarity	NPC151715
0.9029	High Similarity	NPC257430
0.9029	High Similarity	NPC179002
0.9029	High Similarity	NPC187583
0.9	High Similarity	NPC154899
0.9	High Similarity	NPC233396
0.8958	High Similarity	NPC26244
0.8947	High Similarity	NPC162314
0.8947	High Similarity	NPC210497
0.8947	High Similarity	NPC94139
0.8947	High Similarity	NPC306884
0.8947	High Similarity	NPC147284
0.8947	High Similarity	NPC3358
0.8936	High Similarity	NPC312304
0.8922	High Similarity	NPC262365
0.8911	High Similarity	NPC92623
0.8911	High Similarity	NPC135464
0.89	High Similarity	NPC241891
0.8866	High Similarity	NPC216520
0.8866	High Similarity	NPC292730
0.8866	High Similarity	NPC473388
0.8866	High Similarity	NPC82664
0.8866	High Similarity	NPC132271
0.8842	High Similarity	NPC45040
0.8824	High Similarity	NPC61033
0.8824	High Similarity	NPC305603
0.8812	High Similarity	NPC134829
0.88	High Similarity	NPC471228
0.88	High Similarity	NPC235762
0.8788	High Similarity	NPC174911
0.8774	High Similarity	NPC120280
0.875	High Similarity	NPC325292
0.875	High Similarity	NPC138117
0.875	High Similarity	NPC44732
0.8737	High Similarity	NPC300017
0.8725	High Similarity	NPC302681
0.8725	High Similarity	NPC39097
0.8725	High Similarity	NPC109691
0.8725	High Similarity	NPC118286
0.8725	High Similarity	NPC470700
0.8725	High Similarity	NPC39664
0.8723	High Similarity	NPC27974
0.8713	High Similarity	NPC475225
0.87	High Similarity	NPC100340
0.87	High Similarity	NPC143659
0.87	High Similarity	NPC12221
0.8687	High Similarity	NPC92730
0.8679	High Similarity	NPC261343
0.8667	High Similarity	NPC308689
0.866	High Similarity	NPC128062
0.8641	High Similarity	NPC54844
0.8627	High Similarity	NPC246056
0.8614	High Similarity	NPC168829
0.86	High Similarity	NPC130103
0.86	High Similarity	NPC48730
0.86	High Similarity	NPC10588
0.86	High Similarity	NPC248396
0.86	High Similarity	NPC129373
0.8586	High Similarity	NPC32674
0.8586	High Similarity	NPC225464
0.8586	High Similarity	NPC152097
0.8586	High Similarity	NPC156313
0.8585	High Similarity	NPC228425
0.8571	High Similarity	NPC313650
0.8571	High Similarity	NPC132720
0.8571	High Similarity	NPC475018
0.8571	High Similarity	NPC321252
0.8571	High Similarity	NPC252544
0.8571	High Similarity	NPC63345
0.8558	High Similarity	NPC75440
0.8558	High Similarity	NPC11554
0.8557	High Similarity	NPC271440
0.8557	High Similarity	NPC55903
0.8529	High Similarity	NPC30506
0.8529	High Similarity	NPC288411
0.8529	High Similarity	NPC471511
0.8529	High Similarity	NPC102216
0.8526	High Similarity	NPC104216
0.8515	High Similarity	NPC101025
0.8515	High Similarity	NPC110764
0.8515	High Similarity	NPC72947
0.8515	High Similarity	NPC284011
0.8515	High Similarity	NPC471578
0.85	High Similarity	NPC128723
0.85	High Similarity	NPC260775
0.8491	Intermediate Similarity	NPC177576
0.8476	Intermediate Similarity	NPC254833
0.8476	Intermediate Similarity	NPC473524
0.8476	Intermediate Similarity	NPC306045
0.8476	Intermediate Similarity	NPC265211
0.8476	Intermediate Similarity	NPC228343
0.8476	Intermediate Similarity	NPC19808
0.8476	Intermediate Similarity	NPC33728
0.8462	Intermediate Similarity	NPC66834
0.8462	Intermediate Similarity	NPC320439
0.8462	Intermediate Similarity	NPC474352
0.8447	Intermediate Similarity	NPC471350
0.8447	Intermediate Similarity	NPC239291
0.8447	Intermediate Similarity	NPC138942
0.844	Intermediate Similarity	NPC474387
0.844	Intermediate Similarity	NPC247858
0.844	Intermediate Similarity	NPC154511
0.844	Intermediate Similarity	NPC474358
0.844	Intermediate Similarity	NPC257540
0.844	Intermediate Similarity	NPC137496
0.8438	Intermediate Similarity	NPC280347
0.8438	Intermediate Similarity	NPC318325
0.8438	Intermediate Similarity	NPC123273
0.8438	Intermediate Similarity	NPC177420
0.8438	Intermediate Similarity	NPC242240
0.8431	Intermediate Similarity	NPC24404
0.8431	Intermediate Similarity	NPC313030
0.8431	Intermediate Similarity	NPC168393
0.8431	Intermediate Similarity	NPC242342
0.8431	Intermediate Similarity	NPC71002
0.8431	Intermediate Similarity	NPC233827
0.8431	Intermediate Similarity	NPC302219
0.8431	Intermediate Similarity	NPC108497
0.8431	Intermediate Similarity	NPC222522
0.8431	Intermediate Similarity	NPC146798
0.8431	Intermediate Similarity	NPC85479
0.8431	Intermediate Similarity	NPC53051
0.8431	Intermediate Similarity	NPC249828
0.8431	Intermediate Similarity	NPC94351
0.8431	Intermediate Similarity	NPC168303
0.8431	Intermediate Similarity	NPC106396
0.8426	Intermediate Similarity	NPC12656
0.8426	Intermediate Similarity	NPC473137
0.8416	Intermediate Similarity	NPC166761
0.8416	Intermediate Similarity	NPC130756
0.8416	Intermediate Similarity	NPC12931
0.8416	Intermediate Similarity	NPC72729
0.8416	Intermediate Similarity	NPC70677
0.8411	Intermediate Similarity	NPC42911
0.8411	Intermediate Similarity	NPC290353
0.8411	Intermediate Similarity	NPC153795
0.8404	Intermediate Similarity	NPC150837
0.84	Intermediate Similarity	NPC88420
0.84	Intermediate Similarity	NPC475078
0.84	Intermediate Similarity	NPC6597
0.84	Intermediate Similarity	NPC79241
0.84	Intermediate Similarity	NPC291789
0.8384	Intermediate Similarity	NPC222146
0.8381	Intermediate Similarity	NPC174981
0.8378	Intermediate Similarity	NPC109371
0.8378	Intermediate Similarity	NPC470214
0.8378	Intermediate Similarity	NPC470215
0.8365	Intermediate Similarity	NPC54765
0.8365	Intermediate Similarity	NPC155072
0.8365	Intermediate Similarity	NPC113457
0.8364	Intermediate Similarity	NPC200988
0.8364	Intermediate Similarity	NPC145023
0.8364	Intermediate Similarity	NPC175799
0.8364	Intermediate Similarity	NPC610
0.8364	Intermediate Similarity	NPC477136
0.8351	Intermediate Similarity	NPC47950
0.8351	Intermediate Similarity	NPC55561
0.8351	Intermediate Similarity	NPC300478
0.835	Intermediate Similarity	NPC12278
0.835	Intermediate Similarity	NPC8931
0.835	Intermediate Similarity	NPC261573
0.835	Intermediate Similarity	NPC327811
0.835	Intermediate Similarity	NPC120693
0.835	Intermediate Similarity	NPC254965
0.8349	Intermediate Similarity	NPC147179
0.8333	Intermediate Similarity	NPC113460
0.8333	Intermediate Similarity	NPC192032
0.8333	Intermediate Similarity	NPC137415
0.8333	Intermediate Similarity	NPC25493
0.8333	Intermediate Similarity	NPC19680
0.8333	Intermediate Similarity	NPC166313
0.8333	Intermediate Similarity	NPC294186
0.8333	Intermediate Similarity	NPC123175
0.8333	Intermediate Similarity	NPC147310
0.8333	Intermediate Similarity	NPC471485
0.8333	Intermediate Similarity	NPC24407
0.8333	Intermediate Similarity	NPC176730
0.8333	Intermediate Similarity	NPC11280
0.8333	Intermediate Similarity	NPC252105

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 NPC294741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	931
0.2-0.3	1227
0.3-0.4	2773
0.4-0.5	2073
0.5-0.6	1223
0.6-0.7	572
0.7-0.8	104
0.8-0.85	9
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8958	High Similarity	NPD2860	Approved
0.8958	High Similarity	NPD2859	Approved
0.8878	High Similarity	NPD3020	Approved
0.8854	High Similarity	NPD2933	Approved
0.8854	High Similarity	NPD2934	Approved
0.8571	High Similarity	NPD844	Approved
0.8476	Intermediate Similarity	NPD3021	Approved
0.8476	Intermediate Similarity	NPD3022	Approved
0.83	Intermediate Similarity	NPD288	Approved
0.8288	Intermediate Similarity	NPD3091	Approved
0.8283	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1242	Phase 1
0.8235	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2342	Discontinued
0.8073	Intermediate Similarity	NPD7635	Approved
0.8	Intermediate Similarity	NPD845	Approved
0.8	Intermediate Similarity	NPD3092	Approved
0.8	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4750	Phase 3
0.7963	Intermediate Similarity	NPD1792	Phase 2
0.7917	Intermediate Similarity	NPD111	Approved
0.785	Intermediate Similarity	NPD1445	Approved
0.785	Intermediate Similarity	NPD1444	Approved
0.785	Intermediate Similarity	NPD968	Approved
0.7826	Intermediate Similarity	NPD3095	Discontinued
0.7826	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD846	Approved
0.781	Intermediate Similarity	NPD940	Approved
0.7768	Intermediate Similarity	NPD9614	Approved
0.7768	Intermediate Similarity	NPD9618	Approved
0.7736	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD3094	Phase 2
0.7714	Intermediate Similarity	NPD3028	Approved
0.7699	Intermediate Similarity	NPD6671	Approved
0.7679	Intermediate Similarity	NPD2234	Approved
0.7679	Intermediate Similarity	NPD2228	Approved
0.7679	Intermediate Similarity	NPD2229	Approved
0.767	Intermediate Similarity	NPD1809	Phase 2
0.7636	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD9294	Approved
0.7627	Intermediate Similarity	NPD2231	Phase 2
0.7627	Intermediate Similarity	NPD2235	Phase 2
0.7623	Intermediate Similarity	NPD3027	Phase 3
0.7603	Intermediate Similarity	NPD2861	Phase 2
0.7586	Intermediate Similarity	NPD4093	Discontinued
0.7565	Intermediate Similarity	NPD9616	Approved
0.7565	Intermediate Similarity	NPD9615	Approved
0.7565	Intermediate Similarity	NPD9613	Approved
0.7563	Intermediate Similarity	NPD4659	Approved
0.7563	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2684	Approved
0.7522	Intermediate Similarity	NPD5283	Phase 1
0.7521	Intermediate Similarity	NPD3019	Approved
0.7521	Intermediate Similarity	NPD6584	Phase 3
0.7521	Intermediate Similarity	NPD4059	Approved
0.7521	Intermediate Similarity	NPD2286	Discontinued
0.7521	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD316	Approved
0.7479	Intermediate Similarity	NPD2562	Approved
0.7479	Intermediate Similarity	NPD2561	Approved
0.7459	Intermediate Similarity	NPD5736	Approved
0.7438	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4103	Phase 2
0.7407	Intermediate Similarity	NPD9500	Approved
0.7373	Intermediate Similarity	NPD9384	Approved
0.7373	Intermediate Similarity	NPD9381	Approved
0.7368	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1237	Approved
0.7333	Intermediate Similarity	NPD2232	Approved
0.7333	Intermediate Similarity	NPD2233	Approved
0.7333	Intermediate Similarity	NPD2230	Approved
0.7321	Intermediate Similarity	NPD5451	Approved
0.7312	Intermediate Similarity	NPD9087	Approved
0.7304	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1793	Approved
0.7304	Intermediate Similarity	NPD1791	Approved
0.7302	Intermediate Similarity	NPD3059	Approved
0.7302	Intermediate Similarity	NPD3062	Approved
0.7302	Intermediate Similarity	NPD3061	Approved
0.7297	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD290	Approved
0.7295	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7843	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7273	Intermediate Similarity	NPD6582	Phase 2
0.7273	Intermediate Similarity	NPD6583	Phase 3
0.7265	Intermediate Similarity	NPD856	Approved
0.7265	Intermediate Similarity	NPD16	Approved
0.725	Intermediate Similarity	NPD1610	Phase 2
0.725	Intermediate Similarity	NPD1201	Approved
0.7241	Intermediate Similarity	NPD7157	Approved
0.7227	Intermediate Similarity	NPD4589	Approved
0.7227	Intermediate Similarity	NPD5846	Approved
0.7227	Intermediate Similarity	NPD6516	Phase 2
0.7227	Intermediate Similarity	NPD1751	Approved
0.7222	Intermediate Similarity	NPD6407	Approved
0.7222	Intermediate Similarity	NPD6663	Approved
0.7222	Intermediate Similarity	NPD6405	Approved
0.7213	Intermediate Similarity	NPD5310	Approved
0.7213	Intermediate Similarity	NPD5311	Approved
0.7203	Intermediate Similarity	NPD5303	Approved
0.7203	Intermediate Similarity	NPD5304	Approved
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7196	Intermediate Similarity	NPD9273	Approved
0.7188	Intermediate Similarity	NPD9088	Approved
0.7188	Intermediate Similarity	NPD5314	Approved
0.7188	Intermediate Similarity	NPD2568	Approved
0.7182	Intermediate Similarity	NPD9610	Approved
0.7182	Intermediate Similarity	NPD9608	Approved
0.7179	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1980	Approved
0.7167	Intermediate Similarity	NPD1981	Approved
0.7167	Intermediate Similarity	NPD1983	Approved
0.7167	Intermediate Similarity	NPD3421	Phase 3
0.7165	Intermediate Similarity	NPD3620	Phase 2
0.7165	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4060	Phase 1
0.7165	Intermediate Similarity	NPD1613	Approved
0.7165	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2238	Phase 2
0.7155	Intermediate Similarity	NPD2629	Approved
0.7155	Intermediate Similarity	NPD497	Approved
0.7154	Intermediate Similarity	NPD3055	Approved
0.7154	Intermediate Similarity	NPD3053	Approved
0.7143	Intermediate Similarity	NPD1357	Approved
0.7131	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD9622	Approved
0.712	Intermediate Similarity	NPD4908	Phase 1
0.7119	Intermediate Similarity	NPD317	Approved
0.7119	Intermediate Similarity	NPD318	Approved
0.7105	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD709	Approved
0.7083	Intermediate Similarity	NPD4626	Approved
0.7083	Intermediate Similarity	NPD2668	Approved
0.7083	Intermediate Similarity	NPD2667	Approved
0.7077	Intermediate Similarity	NPD7742	Approved
0.7077	Intermediate Similarity	NPD7743	Approved
0.7069	Intermediate Similarity	NPD496	Approved
0.7069	Intermediate Similarity	NPD495	Approved
0.7069	Intermediate Similarity	NPD498	Approved
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.7059	Intermediate Similarity	NPD7330	Discontinued
0.7037	Intermediate Similarity	NPD9495	Approved
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4140	Approved
0.7025	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD3847	Discontinued
0.7016	Intermediate Similarity	NPD1470	Approved
0.7008	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD5585	Approved
0.6992	Remote Similarity	NPD1669	Approved
0.6992	Remote Similarity	NPD4749	Approved
0.6992	Remote Similarity	NPD1755	Approved
0.6992	Remote Similarity	NPD5327	Phase 3
0.6983	Remote Similarity	NPD821	Approved
0.6983	Remote Similarity	NPD5535	Approved
0.6977	Remote Similarity	NPD5735	Approved
0.697	Remote Similarity	NPD7266	Discontinued
0.697	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.696	Remote Similarity	NPD9621	Approved
0.696	Remote Similarity	NPD9619	Approved
0.696	Remote Similarity	NPD2195	Approved
0.696	Remote Similarity	NPD4624	Approved
0.696	Remote Similarity	NPD858	Approved
0.696	Remote Similarity	NPD2194	Approved
0.696	Remote Similarity	NPD859	Approved
0.696	Remote Similarity	NPD9620	Approved
0.696	Remote Similarity	NPD599	Approved
0.696	Remote Similarity	NPD602	Approved
0.6957	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2557	Approved
0.6937	Remote Similarity	NPD4658	Approved
0.6937	Remote Similarity	NPD4656	Approved
0.6935	Remote Similarity	NPD1283	Approved
0.6929	Remote Similarity	NPD5156	Approved
0.6929	Remote Similarity	NPD5155	Approved
0.6923	Remote Similarity	NPD817	Approved
0.6923	Remote Similarity	NPD823	Approved
0.6917	Remote Similarity	NPD1182	Approved
0.6917	Remote Similarity	NPD1894	Discontinued
0.6911	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1608	Approved
0.6909	Remote Similarity	NPD2550	Approved
0.6909	Remote Similarity	NPD2552	Approved
0.6909	Remote Similarity	NPD2553	Approved
0.6909	Remote Similarity	NPD2555	Approved
0.6909	Remote Similarity	NPD2549	Approved
0.6909	Remote Similarity	NPD2558	Approved
0.6909	Remote Similarity	NPD1616	Discontinued
0.6905	Remote Similarity	NPD3637	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