NPASS Compound

Structure

CID252105 OpenBabel06191716052D 26 26 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 2.8660 -0.2321 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 1.8660 3.2321 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 2.3660 0.6340 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 0.8660 3.2321 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 -6.9282 -0.0000 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 -5.1962 -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 -3.4641 -0.0000 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 1.0000 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 1.3660 0.6340 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 0.3660 2.3660 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 -1.7321 -0.0000 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 0.0000 -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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 2 0 0 0 0 3 7 2 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.29
Volume:	425.371
LogP:	8.647
LogD:	5.07
LogS:	-6.745
# Rotatable Bonds:	15
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	2.923
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	1.2632021025638096e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.617
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	101.56985473632812%
Volume Distribution (VD):	0.443
Pgp-substrate:	0.34726375341415405%

ADMET: Metabolism

CYP1A2-inhibitor:	0.42
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.202
CYP2C9-inhibitor:	0.386
CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	5.252
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.741
Carcinogencity:	0.11
Eye Corrosion:	0.04
Eye Irritation:	0.965
Respiratory Toxicity:	0.417

Download Data

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

Natural Product: NPC252105

Natural Product ID:	NPC252105
*Common Name:**	2-(1,1-Diallylbut-3-Enyl)-5-Nonylphenol
IUPAC Name:	5-nonyl-2-(4-prop-2-enylhepta-1,6-dien-4-yl)phenol
Synonyms:
Standard InCHIKey:	KQGCECAJFLDXBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H38O/c1-5-9-10-11-12-13-14-15-22-16-17-23(24(26)21-22)25(18-6-2,19-7-3)20-8-4/h6-8,16-17,21,26H,2-5,9-15,18-20H2,1H3
SMILES:	CCCCCCCCCc1ccc(c(c1)O)C(CC=C)(CC=C)CC=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104962
PubChem CID:	76317396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO32453	Streptomyces sp. TC1	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24387661]

☑ 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
Others	6

Activity Type	# Activity
NON-MOLECULAR	5
Others	1
Uncleic Acid	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1514	Uncleic Acid	DNA	Bos taurus	Kapp	=	0.34	10'5/M	PMID[543644]
NPT1514	Uncleic Acid	DNA	Bos taurus	Kq	=	0.68	10'4/M	PMID[543644]
NPT1514	Uncleic Acid	DNA	Bos taurus	Kb	=	2.23	10'4/M	PMID[543644]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32800.0	nM	PMID[543644]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31100.0	nM	PMID[543644]
NPT1	Others	Radical scavenging activity		IC50	=	14900.0	nM	PMID[543644]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	4016.9	umol/g	PMID[543644]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8.4	mg/g	PMID[543644]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	4373.3	mmol/g	PMID[543644]

☑ 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 NPC252105 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	309
0.1-0.2	1803
0.2-0.3	4132
0.3-0.4	13263
0.4-0.5	7682
0.5-0.6	10430
0.6-0.7	3884
0.7-0.8	866
0.8-0.85	206
0.85-0.9	85
0.9-0.95	32
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC299762
0.9787	High Similarity	NPC33675
0.949	High Similarity	NPC47284
0.9474	High Similarity	NPC79241
0.9474	High Similarity	NPC6597
0.9394	High Similarity	NPC53740
0.9368	High Similarity	NPC259512
0.9368	High Similarity	NPC312132
0.9362	High Similarity	NPC152415
0.9278	High Similarity	NPC72729
0.9255	High Similarity	NPC3358
0.9255	High Similarity	NPC210497
0.9255	High Similarity	NPC55903
0.9255	High Similarity	NPC306884
0.9255	High Similarity	NPC147284
0.9255	High Similarity	NPC162314
0.9255	High Similarity	NPC94139
0.92	High Similarity	NPC310456
0.9184	High Similarity	NPC477685
0.9149	High Similarity	NPC306074
0.9149	High Similarity	NPC231150
0.9082	High Similarity	NPC48730
0.9082	High Similarity	NPC129373
0.9082	High Similarity	NPC248396
0.9082	High Similarity	NPC225506
0.9062	High Similarity	NPC222146
0.9043	High Similarity	NPC192
0.902	High Similarity	NPC306295
0.902	High Similarity	NPC64586
0.901	High Similarity	NPC155072
0.9	High Similarity	NPC475225
0.899	High Similarity	NPC80800
0.898	High Similarity	NPC260775
0.898	High Similarity	NPC252821
0.898	High Similarity	NPC122005
0.8958	High Similarity	NPC316301
0.8958	High Similarity	NPC289769
0.8958	High Similarity	NPC27323
0.8958	High Similarity	NPC245187
0.8922	High Similarity	NPC204901
0.8922	High Similarity	NPC158253
0.8922	High Similarity	NPC320439
0.8922	High Similarity	NPC232523
0.8911	High Similarity	NPC117115
0.89	High Similarity	NPC269212
0.89	High Similarity	NPC235762
0.89	High Similarity	NPC471228
0.8889	High Similarity	NPC130756
0.8889	High Similarity	NPC174911
0.8889	High Similarity	NPC70677
0.8889	High Similarity	NPC12931
0.8878	High Similarity	NPC152097
0.8866	High Similarity	NPC32714
0.8857	High Similarity	NPC177962
0.8857	High Similarity	NPC62867
0.8857	High Similarity	NPC250323
0.883	High Similarity	NPC27974
0.8824	High Similarity	NPC12640
0.8824	High Similarity	NPC201662
0.8824	High Similarity	NPC99836
0.8763	High Similarity	NPC76938
0.8762	High Similarity	NPC266937
0.8762	High Similarity	NPC77772
0.8762	High Similarity	NPC470770
0.8762	High Similarity	NPC260323
0.8762	High Similarity	NPC176279
0.875	High Similarity	NPC155908
0.8738	High Similarity	NPC66834
0.8738	High Similarity	NPC151477
0.8725	High Similarity	NPC37802
0.8723	High Similarity	NPC407
0.8723	High Similarity	NPC307235
0.8713	High Similarity	NPC108497
0.87	High Similarity	NPC211885
0.8692	High Similarity	NPC195922
0.8687	High Similarity	NPC225464
0.8687	High Similarity	NPC475078
0.8687	High Similarity	NPC77492
0.8673	High Similarity	NPC144682
0.8667	High Similarity	NPC141782
0.8667	High Similarity	NPC13482
0.8646	High Similarity	NPC55561
0.8641	High Similarity	NPC21594
0.8641	High Similarity	NPC477814
0.8627	High Similarity	NPC227458
0.8627	High Similarity	NPC238696
0.8627	High Similarity	NPC218879
0.8627	High Similarity	NPC244513
0.8627	High Similarity	NPC272029
0.8617	High Similarity	NPC155393
0.86	High Similarity	NPC92730
0.8585	High Similarity	NPC224527
0.8585	High Similarity	NPC469912
0.8571	High Similarity	NPC33728
0.8571	High Similarity	NPC299568
0.8571	High Similarity	NPC19808
0.8571	High Similarity	NPC58865
0.8571	High Similarity	NPC186385
0.8558	High Similarity	NPC474352
0.8557	High Similarity	NPC304541
0.8542	High Similarity	NPC242240
0.8542	High Similarity	NPC98772
0.8542	High Similarity	NPC177420
0.8542	High Similarity	NPC318325
0.8542	High Similarity	NPC123273
0.8542	High Similarity	NPC280347
0.8532	High Similarity	NPC471668
0.8532	High Similarity	NPC141001
0.8529	High Similarity	NPC242342
0.8529	High Similarity	NPC302219
0.8529	High Similarity	NPC94351
0.8529	High Similarity	NPC222522
0.8529	High Similarity	NPC85479
0.8529	High Similarity	NPC24404
0.8529	High Similarity	NPC146798
0.8529	High Similarity	NPC249828
0.8529	High Similarity	NPC313030
0.8529	High Similarity	NPC71002
0.8529	High Similarity	NPC168303
0.8529	High Similarity	NPC106396
0.8529	High Similarity	NPC53051
0.8511	High Similarity	NPC286904
0.8511	High Similarity	NPC150837
0.8505	High Similarity	NPC228425
0.8505	High Similarity	NPC228452
0.8505	High Similarity	NPC166995
0.8505	High Similarity	NPC302371
0.8505	High Similarity	NPC46940
0.85	High Similarity	NPC474073
0.85	High Similarity	NPC156313
0.8491	Intermediate Similarity	NPC132720
0.8485	Intermediate Similarity	NPC8392
0.8476	Intermediate Similarity	NPC174981
0.8469	Intermediate Similarity	NPC29373
0.8469	Intermediate Similarity	NPC271440
0.8462	Intermediate Similarity	NPC469913
0.8455	Intermediate Similarity	NPC477136
0.8455	Intermediate Similarity	NPC320864
0.8447	Intermediate Similarity	NPC120719
0.8447	Intermediate Similarity	NPC475580
0.844	Intermediate Similarity	NPC192948
0.844	Intermediate Similarity	NPC469719
0.844	Intermediate Similarity	NPC35797
0.8438	Intermediate Similarity	NPC19680
0.8438	Intermediate Similarity	NPC113460
0.8438	Intermediate Similarity	NPC25493
0.8431	Intermediate Similarity	NPC11280
0.8431	Intermediate Similarity	NPC147310
0.8431	Intermediate Similarity	NPC72947
0.8431	Intermediate Similarity	NPC137415
0.8431	Intermediate Similarity	NPC192032
0.8431	Intermediate Similarity	NPC12221
0.8431	Intermediate Similarity	NPC284011
0.8431	Intermediate Similarity	NPC294186
0.8431	Intermediate Similarity	NPC166313
0.8431	Intermediate Similarity	NPC24407
0.8426	Intermediate Similarity	NPC263753
0.8426	Intermediate Similarity	NPC715
0.8426	Intermediate Similarity	NPC23804
0.8411	Intermediate Similarity	NPC95716
0.8411	Intermediate Similarity	NPC322753
0.8411	Intermediate Similarity	NPC275627
0.8411	Intermediate Similarity	NPC54373
0.8378	Intermediate Similarity	NPC206
0.8367	Intermediate Similarity	NPC204210
0.8367	Intermediate Similarity	NPC270547
0.8365	Intermediate Similarity	NPC138942
0.8365	Intermediate Similarity	NPC99557
0.8365	Intermediate Similarity	NPC219286
0.8364	Intermediate Similarity	NPC469663
0.8364	Intermediate Similarity	NPC477137
0.8364	Intermediate Similarity	NPC219112
0.8364	Intermediate Similarity	NPC92
0.8364	Intermediate Similarity	NPC38893
0.8364	Intermediate Similarity	NPC308311
0.8351	Intermediate Similarity	NPC258219
0.835	Intermediate Similarity	NPC196479
0.835	Intermediate Similarity	NPC168829
0.8349	Intermediate Similarity	NPC471534
0.8349	Intermediate Similarity	NPC268160
0.8333	Intermediate Similarity	NPC166761
0.8333	Intermediate Similarity	NPC184169
0.8333	Intermediate Similarity	NPC23167
0.8333	Intermediate Similarity	NPC10588
0.8333	Intermediate Similarity	NPC294741
0.8318	Intermediate Similarity	NPC296683
0.8304	Intermediate Similarity	NPC93071
0.8304	Intermediate Similarity	NPC126002
0.8304	Intermediate Similarity	NPC471449
0.8302	Intermediate Similarity	NPC11554
0.83	Intermediate Similarity	NPC26244
0.83	Intermediate Similarity	NPC274678
0.8288	Intermediate Similarity	NPC172219
0.8288	Intermediate Similarity	NPC304510
0.8286	Intermediate Similarity	NPC271274
0.8273	Intermediate Similarity	NPC84999
0.8273	Intermediate Similarity	NPC147179
0.8273	Intermediate Similarity	NPC246760
0.8269	Intermediate Similarity	NPC288411
0.8269	Intermediate Similarity	NPC323810

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 NPC252105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1028
0.2-0.3	1382
0.3-0.4	2950
0.4-0.5	1906
0.5-0.6	1109
0.6-0.7	371
0.7-0.8	64
0.8-0.85	11
0.85-0.9	3
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9468	High Similarity	NPD844	Approved
0.9368	High Similarity	NPD288	Approved
0.9082	High Similarity	NPD289	Clinical (unspecified phase)
0.8958	High Similarity	NPD1432	Clinical (unspecified phase)
0.8673	High Similarity	NPD1809	Phase 2
0.866	High Similarity	NPD845	Approved
0.8571	High Similarity	NPD4750	Phase 3
0.8505	High Similarity	NPD7635	Approved
0.8416	Intermediate Similarity	NPD3020	Approved
0.8381	Intermediate Similarity	NPD2342	Discontinued
0.83	Intermediate Similarity	NPD2859	Approved
0.83	Intermediate Similarity	NPD2860	Approved
0.82	Intermediate Similarity	NPD2933	Approved
0.82	Intermediate Similarity	NPD2934	Approved
0.8113	Intermediate Similarity	NPD1444	Approved
0.8113	Intermediate Similarity	NPD1445	Approved
0.8077	Intermediate Similarity	NPD846	Approved
0.8077	Intermediate Similarity	NPD940	Approved
0.8056	Intermediate Similarity	NPD3021	Approved
0.8056	Intermediate Similarity	NPD3022	Approved
0.8021	Intermediate Similarity	NPD111	Approved
0.7946	Intermediate Similarity	NPD6671	Approved
0.7909	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3091	Approved
0.789	Intermediate Similarity	NPD1792	Phase 2
0.7857	Intermediate Similarity	NPD1791	Approved
0.7857	Intermediate Similarity	NPD1793	Approved
0.7768	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3019	Approved
0.7759	Intermediate Similarity	NPD2932	Approved
0.7759	Intermediate Similarity	NPD4059	Approved
0.7731	Intermediate Similarity	NPD6696	Suspended
0.7627	Intermediate Similarity	NPD3092	Approved
0.7627	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4626	Approved
0.7607	Intermediate Similarity	NPD1751	Approved
0.7607	Intermediate Similarity	NPD4589	Approved
0.7603	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9500	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1242	Phase 1
0.7458	Intermediate Similarity	NPD3095	Discontinued
0.7456	Intermediate Similarity	NPD2229	Approved
0.7456	Intermediate Similarity	NPD2234	Approved
0.7456	Intermediate Similarity	NPD2228	Approved
0.7436	Intermediate Similarity	NPD7330	Discontinued
0.7398	Intermediate Similarity	NPD5736	Approved
0.7391	Intermediate Similarity	NPD497	Approved
0.7377	Intermediate Similarity	NPD3094	Phase 2
0.7373	Intermediate Similarity	NPD4093	Discontinued
0.7355	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7157	Approved
0.7317	Intermediate Similarity	NPD2194	Approved
0.7317	Intermediate Similarity	NPD2195	Approved
0.7311	Intermediate Similarity	NPD2286	Discontinued
0.7311	Intermediate Similarity	NPD1778	Approved
0.7304	Intermediate Similarity	NPD495	Approved
0.7304	Intermediate Similarity	NPD498	Approved
0.7304	Intermediate Similarity	NPD496	Approved
0.729	Intermediate Similarity	NPD9273	Approved
0.7288	Intermediate Similarity	NPD5304	Approved
0.7288	Intermediate Similarity	NPD5303	Approved
0.7281	Intermediate Similarity	NPD228	Approved
0.728	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD9610	Approved
0.7273	Intermediate Similarity	NPD9608	Approved
0.7265	Intermediate Similarity	NPD7340	Approved
0.7265	Intermediate Similarity	NPD7636	Approved
0.7258	Intermediate Similarity	NPD3636	Approved
0.7258	Intermediate Similarity	NPD3637	Approved
0.7258	Intermediate Similarity	NPD3635	Approved
0.725	Intermediate Similarity	NPD1981	Approved
0.725	Intermediate Similarity	NPD1983	Approved
0.725	Intermediate Similarity	NPD1980	Approved
0.7234	Intermediate Similarity	NPD9087	Approved
0.7227	Intermediate Similarity	NPD5691	Approved
0.7227	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1755	Approved
0.72	Intermediate Similarity	NPD2605	Approved
0.72	Intermediate Similarity	NPD2606	Approved
0.719	Intermediate Similarity	NPD1201	Approved
0.7182	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6663	Approved
0.7156	Intermediate Similarity	NPD3028	Approved
0.7155	Intermediate Similarity	NPD1398	Phase 1
0.7143	Intermediate Similarity	NPD5155	Approved
0.7143	Intermediate Similarity	NPD5156	Approved
0.7132	Intermediate Similarity	NPD4097	Suspended
0.7131	Intermediate Similarity	NPD2230	Approved
0.7131	Intermediate Similarity	NPD2232	Approved
0.7131	Intermediate Similarity	NPD2233	Approved
0.7119	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3023	Approved
0.7107	Intermediate Similarity	NPD3143	Discontinued
0.7107	Intermediate Similarity	NPD3026	Approved
0.7107	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3496	Discontinued
0.7099	Intermediate Similarity	NPD6100	Approved
0.7099	Intermediate Similarity	NPD6099	Approved
0.7094	Intermediate Similarity	NPD9618	Approved
0.7094	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9614	Approved
0.7083	Intermediate Similarity	NPD3024	Approved
0.7083	Intermediate Similarity	NPD3025	Approved
0.7069	Intermediate Similarity	NPD9379	Approved
0.7069	Intermediate Similarity	NPD9377	Approved
0.7063	Intermediate Similarity	NPD3594	Approved
0.7063	Intermediate Similarity	NPD3595	Approved
0.704	Intermediate Similarity	NPD4624	Approved
0.7034	Intermediate Similarity	NPD709	Approved
0.7018	Intermediate Similarity	NPD2684	Approved
0.701	Intermediate Similarity	NPD9294	Approved
0.7009	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD1616	Discontinued
0.6992	Remote Similarity	NPD3070	Discontinued
0.6984	Remote Similarity	NPD2861	Phase 2
0.6977	Remote Similarity	NPD6346	Approved
0.696	Remote Similarity	NPD1470	Approved
0.696	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9088	Approved
0.6937	Remote Similarity	NPD4818	Approved
0.6937	Remote Similarity	NPD4817	Approved
0.6935	Remote Similarity	NPD5327	Phase 3
0.693	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD7843	Approved
0.6917	Remote Similarity	NPD9615	Approved
0.6917	Remote Similarity	NPD9613	Approved
0.6917	Remote Similarity	NPD9616	Approved
0.6894	Remote Similarity	NPD7742	Approved
0.6894	Remote Similarity	NPD7743	Approved
0.6889	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7095	Approved
0.686	Remote Similarity	NPD316	Approved
0.6846	Remote Similarity	NPD4060	Phase 1
0.6846	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3620	Phase 2
0.6842	Remote Similarity	NPD968	Approved
0.6822	Remote Similarity	NPD1088	Approved
0.6818	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD475	Phase 2
0.6803	Remote Similarity	NPD1651	Approved
0.6803	Remote Similarity	NPD1357	Approved
0.6797	Remote Similarity	NPD4908	Phase 1
0.6794	Remote Similarity	NPD5735	Approved
0.678	Remote Similarity	NPD1138	Approved
0.6774	Remote Similarity	NPD1610	Phase 2
0.6774	Remote Similarity	NPD1611	Approved
0.6772	Remote Similarity	NPD6584	Phase 3
0.6762	Remote Similarity	NPD1101	Approved
0.6752	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.675	Remote Similarity	NPD255	Approved
0.675	Remote Similarity	NPD256	Approved
0.675	Remote Similarity	NPD6387	Discontinued
0.6748	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2668	Approved
0.6748	Remote Similarity	NPD2667	Approved
0.6746	Remote Similarity	NPD1283	Approved
0.6746	Remote Similarity	NPD5310	Approved
0.6746	Remote Similarity	NPD8651	Approved
0.6746	Remote Similarity	NPD5311	Approved
0.6742	Remote Similarity	NPD6353	Approved
0.6741	Remote Similarity	NPD4256	Phase 2
0.6741	Remote Similarity	NPD4257	Approved
0.6724	Remote Similarity	NPD74	Approved
0.6724	Remote Similarity	NPD9266	Approved
0.6723	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1759	Phase 1
0.6719	Remote Similarity	NPD1712	Approved
0.6719	Remote Similarity	NPD4208	Discontinued
0.6719	Remote Similarity	NPD4212	Discontinued
0.6718	Remote Similarity	NPD4140	Approved
0.6695	Remote Similarity	NPD1139	Approved
0.6695	Remote Similarity	NPD1137	Approved
0.6694	Remote Similarity	NPD9493	Approved
0.6693	Remote Similarity	NPD3053	Approved
0.6693	Remote Similarity	NPD3055	Approved
0.6693	Remote Similarity	NPD2797	Approved
0.6692	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2209	Approved
0.6691	Remote Similarity	NPD2211	Approved
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD3445	Approved
0.6667	Remote Similarity	NPD9244	Approved
0.6667	Remote Similarity	NPD9089	Approved
0.6667	Remote Similarity	NPD4725	Approved
0.6667	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD4726	Approved
0.6667	Remote Similarity	NPD3444	Approved
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD4207	Discontinued
0.6667	Remote Similarity	NPD3443	Approved
0.6667	Remote Similarity	NPD5951	Approved
0.6642	Remote Similarity	NPD8166	Discontinued
0.6642	Remote Similarity	NPD3299	Clinical (unspecified phase)

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