NPASS Compound

Structure

CID320439 OpenBabel06191716152D 23 24 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -0.8660 1.5000 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 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 1 15 1 0 0 0 0 2 16 2 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	359.057
LogP:	5.345
LogD:	4.65
LogS:	-4.376
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	3.38
Fsp3:	0.524
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:	-4.77
MDCK Permeability:	2.006539943977259e-05
Pgp-inhibitor:	0.91
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.35

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	98.44660949707031%
Volume Distribution (VD):	0.773
Pgp-substrate:	0.8061829209327698%

ADMET: Metabolism

CYP1A2-inhibitor:	0.346
CYP1A2-substrate:	0.601
CYP2C19-inhibitor:	0.734
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.48
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.371
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	6.81
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.855
Carcinogencity:	0.027
Eye Corrosion:	0.052
Eye Irritation:	0.937
Respiratory Toxicity:	0.79

Download Data

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

Natural Product: NPC320439

Natural Product ID:	NPC320439
*Common Name:**	Metachromin V
IUPAC Name:	2-[(E)-5-(2,2-dimethyl-6-methylidenecyclohexyl)-3-methylpent-2-enyl]benzene-1,4-diol
Synonyms:	Metachromin V
Standard InCHIKey:	JJJNVPBHJYTLFL-VIZOYTHASA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-15(7-9-17-14-18(22)10-12-20(17)23)8-11-19-16(2)6-5-13-21(19,3)4/h7,10,12,14,19,22-23H,2,5-6,8-9,11,13H2,1,3-4H3/b15-7+
SMILES:	C/C(=CCc1cc(O)ccc1O)/CCC1C(=C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784271
PubChem CID:	53262705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO24805	Thorecta reticulata	Species	Thorectidae	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
GI50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	5100.0	nM	PMID[469597]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	3200.0	nM	PMID[469597]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	5100.0	nM	PMID[469597]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	10000.0	nM	PMID[469597]
NPT913	Cell Line	CHO-K1	Cricetulus griseus	GI50	=	2100.0	nM	PMID[469597]

☑ 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 NPC320439 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	290
0.1-0.2	1579
0.2-0.3	3440
0.3-0.4	11303
0.4-0.5	8664
0.5-0.6	11283
0.6-0.7	4868
0.7-0.8	994
0.8-0.85	185
0.85-0.9	75
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC77772
0.9612	High Similarity	NPC266937
0.9612	High Similarity	NPC470770
0.9519	High Similarity	NPC177962
0.9519	High Similarity	NPC62867
0.9505	High Similarity	NPC155072
0.9406	High Similarity	NPC47284
0.9314	High Similarity	NPC53740
0.93	High Similarity	NPC12221
0.9208	High Similarity	NPC269212
0.92	High Similarity	NPC248396
0.92	High Similarity	NPC129373
0.92	High Similarity	NPC48730
0.9192	High Similarity	NPC152097
0.9167	High Similarity	NPC141001
0.9159	High Similarity	NPC471534
0.9118	High Similarity	NPC475580
0.91	High Similarity	NPC260775
0.902	High Similarity	NPC108497
0.902	High Similarity	NPC233827
0.901	High Similarity	NPC130756
0.901	High Similarity	NPC70677
0.901	High Similarity	NPC12931
0.9	High Similarity	NPC475078
0.8962	High Similarity	NPC13482
0.8922	High Similarity	NPC252105
0.8922	High Similarity	NPC477685
0.8919	High Similarity	NPC323074
0.8911	High Similarity	NPC299762
0.8911	High Similarity	NPC33675
0.8889	High Similarity	NPC152415
0.8879	High Similarity	NPC54373
0.8846	High Similarity	NPC117115
0.8839	High Similarity	NPC318581
0.8839	High Similarity	NPC325544
0.8839	High Similarity	NPC477037
0.8824	High Similarity	NPC72729
0.8812	High Similarity	NPC6597
0.8812	High Similarity	NPC79241
0.8796	High Similarity	NPC228425
0.8796	High Similarity	NPC250323
0.8788	High Similarity	NPC55903
0.8788	High Similarity	NPC29373
0.8785	High Similarity	NPC141782
0.8785	High Similarity	NPC132720
0.8762	High Similarity	NPC67250
0.8762	High Similarity	NPC469913
0.8762	High Similarity	NPC54765
0.875	High Similarity	NPC272029
0.875	High Similarity	NPC475225
0.875	High Similarity	NPC323810
0.8738	High Similarity	NPC80800
0.8725	High Similarity	NPC92730
0.8713	High Similarity	NPC312132
0.8713	High Similarity	NPC259512
0.8704	High Similarity	NPC469912
0.8704	High Similarity	NPC176279
0.8704	High Similarity	NPC275627
0.8704	High Similarity	NPC260323
0.87	High Similarity	NPC245187
0.87	High Similarity	NPC76938
0.8687	High Similarity	NPC306074
0.8679	High Similarity	NPC151477
0.8667	High Similarity	NPC138942
0.8654	High Similarity	NPC471228
0.8654	High Similarity	NPC235762
0.8649	High Similarity	NPC308828
0.8649	High Similarity	NPC92
0.8649	High Similarity	NPC469663
0.8641	High Similarity	NPC225506
0.8636	High Similarity	NPC268160
0.8636	High Similarity	NPC195922
0.8627	High Similarity	NPC225464
0.8627	High Similarity	NPC156313
0.8624	High Similarity	NPC302371
0.8614	High Similarity	NPC222146
0.8614	High Similarity	NPC32714
0.86	High Similarity	NPC306884
0.86	High Similarity	NPC147284
0.86	High Similarity	NPC94139
0.86	High Similarity	NPC162314
0.86	High Similarity	NPC3358
0.86	High Similarity	NPC210497
0.8598	High Similarity	NPC64586
0.8598	High Similarity	NPC11554
0.8598	High Similarity	NPC95344
0.8586	High Similarity	NPC192
0.8585	High Similarity	NPC310456
0.8571	High Similarity	NPC477136
0.8571	High Similarity	NPC288411
0.8559	High Similarity	NPC192948
0.8559	High Similarity	NPC147179
0.8559	High Similarity	NPC35797
0.8559	High Similarity	NPC469719
0.8544	High Similarity	NPC122005
0.8544	High Similarity	NPC252821
0.8532	High Similarity	NPC95716
0.8532	High Similarity	NPC322753
0.8532	High Similarity	NPC224527
0.8529	High Similarity	NPC216520
0.8529	High Similarity	NPC132271
0.8529	High Similarity	NPC473388
0.8529	High Similarity	NPC292730
0.8529	High Similarity	NPC82664
0.8519	High Similarity	NPC58865
0.8515	High Similarity	NPC289769
0.8515	High Similarity	NPC27323
0.8515	High Similarity	NPC316301
0.8505	High Similarity	NPC66834
0.8496	Intermediate Similarity	NPC469609
0.8482	Intermediate Similarity	NPC477137
0.8482	Intermediate Similarity	NPC154511
0.8482	Intermediate Similarity	NPC474358
0.8482	Intermediate Similarity	NPC38893
0.8482	Intermediate Similarity	NPC474387
0.8482	Intermediate Similarity	NPC471668
0.8482	Intermediate Similarity	NPC137496
0.8482	Intermediate Similarity	NPC219112
0.8482	Intermediate Similarity	NPC247858
0.8482	Intermediate Similarity	NPC308311
0.8482	Intermediate Similarity	NPC257540
0.8476	Intermediate Similarity	NPC168829
0.8476	Intermediate Similarity	NPC168393
0.8462	Intermediate Similarity	NPC130103
0.8462	Intermediate Similarity	NPC211885
0.8462	Intermediate Similarity	NPC248557
0.8462	Intermediate Similarity	NPC174911
0.8462	Intermediate Similarity	NPC294741
0.8455	Intermediate Similarity	NPC46940
0.8455	Intermediate Similarity	NPC98372
0.8447	Intermediate Similarity	NPC77492
0.8447	Intermediate Similarity	NPC474073
0.844	Intermediate Similarity	NPC296683
0.8431	Intermediate Similarity	NPC274678
0.8431	Intermediate Similarity	NPC26244
0.8426	Intermediate Similarity	NPC306295
0.8426	Intermediate Similarity	NPC279887
0.8426	Intermediate Similarity	NPC68260
0.8421	Intermediate Similarity	NPC469644
0.8421	Intermediate Similarity	NPC471449
0.8416	Intermediate Similarity	NPC271440
0.8411	Intermediate Similarity	NPC477814
0.8411	Intermediate Similarity	NPC21594
0.8411	Intermediate Similarity	NPC271274
0.8407	Intermediate Similarity	NPC320864
0.8407	Intermediate Similarity	NPC304510
0.8407	Intermediate Similarity	NPC16030
0.8407	Intermediate Similarity	NPC172219
0.8396	Intermediate Similarity	NPC238696
0.8393	Intermediate Similarity	NPC84999
0.8393	Intermediate Similarity	NPC246760
0.8384	Intermediate Similarity	NPC27974
0.8381	Intermediate Similarity	NPC51015
0.8378	Intermediate Similarity	NPC715
0.8364	Intermediate Similarity	NPC151537
0.8349	Intermediate Similarity	NPC254833
0.8349	Intermediate Similarity	NPC19808
0.8349	Intermediate Similarity	NPC186385
0.8349	Intermediate Similarity	NPC299568
0.8349	Intermediate Similarity	NPC33728
0.8349	Intermediate Similarity	NPC228343
0.8349	Intermediate Similarity	NPC473524
0.8349	Intermediate Similarity	NPC26013
0.8349	Intermediate Similarity	NPC98392
0.8349	Intermediate Similarity	NPC282855
0.8348	Intermediate Similarity	NPC260832
0.8348	Intermediate Similarity	NPC135467
0.8333	Intermediate Similarity	NPC474352
0.8333	Intermediate Similarity	NPC128062
0.8333	Intermediate Similarity	NPC206
0.8333	Intermediate Similarity	NPC151715
0.8333	Intermediate Similarity	NPC233320
0.8333	Intermediate Similarity	NPC471671
0.8318	Intermediate Similarity	NPC219286
0.8318	Intermediate Similarity	NPC99557
0.8317	Intermediate Similarity	NPC155908
0.8317	Intermediate Similarity	NPC231150
0.8317	Intermediate Similarity	NPC304541
0.8304	Intermediate Similarity	NPC107240
0.8288	Intermediate Similarity	NPC228452
0.8283	Intermediate Similarity	NPC407
0.8283	Intermediate Similarity	NPC307235
0.8276	Intermediate Similarity	NPC32322
0.8276	Intermediate Similarity	NPC241001
0.8276	Intermediate Similarity	NPC164852
0.8276	Intermediate Similarity	NPC129176
0.8276	Intermediate Similarity	NPC259703
0.8273	Intermediate Similarity	NPC208229
0.8269	Intermediate Similarity	NPC32674
0.8269	Intermediate Similarity	NPC88420
0.8261	Intermediate Similarity	NPC93071
0.8261	Intermediate Similarity	NPC51341
0.8261	Intermediate Similarity	NPC126002
0.8261	Intermediate Similarity	NPC151197
0.8257	Intermediate Similarity	NPC174981
0.8257	Intermediate Similarity	NPC262365
0.8252	Intermediate Similarity	NPC144682
0.8252	Intermediate Similarity	NPC8392
0.823	Intermediate Similarity	NPC232165
0.8224	Intermediate Similarity	NPC102216

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 NPC320439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	973
0.2-0.3	1161
0.3-0.4	2922
0.4-0.5	2029
0.5-0.6	1297
0.6-0.7	394
0.7-0.8	78
0.8-0.85	16
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9394	High Similarity	NPD289	Clinical (unspecified phase)
0.8972	High Similarity	NPD7635	Approved
0.8725	High Similarity	NPD3020	Approved
0.8713	High Similarity	NPD288	Approved
0.8614	High Similarity	NPD844	Approved
0.8515	High Similarity	NPD1432	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD2860	Approved
0.8431	Intermediate Similarity	NPD2859	Approved
0.8416	Intermediate Similarity	NPD845	Approved
0.8349	Intermediate Similarity	NPD3021	Approved
0.8349	Intermediate Similarity	NPD3022	Approved
0.8349	Intermediate Similarity	NPD4750	Phase 3
0.8333	Intermediate Similarity	NPD2934	Approved
0.8333	Intermediate Similarity	NPD2933	Approved
0.8252	Intermediate Similarity	NPD1809	Phase 2
0.823	Intermediate Similarity	NPD6671	Approved
0.8182	Intermediate Similarity	NPD1792	Phase 2
0.8174	Intermediate Similarity	NPD3091	Approved
0.8165	Intermediate Similarity	NPD2342	Discontinued
0.8034	Intermediate Similarity	NPD4059	Approved
0.8034	Intermediate Similarity	NPD3019	Approved
0.8034	Intermediate Similarity	NPD2932	Approved
0.7909	Intermediate Similarity	NPD1444	Approved
0.7909	Intermediate Similarity	NPD1445	Approved
0.7899	Intermediate Similarity	NPD3092	Approved
0.787	Intermediate Similarity	NPD846	Approved
0.787	Intermediate Similarity	NPD940	Approved
0.7826	Intermediate Similarity	NPD497	Approved
0.7787	Intermediate Similarity	NPD3094	Phase 2
0.7769	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD2229	Approved
0.7739	Intermediate Similarity	NPD495	Approved
0.7739	Intermediate Similarity	NPD498	Approved
0.7739	Intermediate Similarity	NPD2234	Approved
0.7739	Intermediate Similarity	NPD2228	Approved
0.7739	Intermediate Similarity	NPD496	Approved
0.7731	Intermediate Similarity	NPD3095	Discontinued
0.7731	Intermediate Similarity	NPD1751	Approved
0.7712	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6696	Suspended
0.7686	Intermediate Similarity	NPD2232	Approved
0.7686	Intermediate Similarity	NPD2233	Approved
0.7686	Intermediate Similarity	NPD2230	Approved
0.7661	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD4093	Discontinued
0.7624	Intermediate Similarity	NPD111	Approved
0.7615	Intermediate Similarity	NPD1242	Phase 1
0.7583	Intermediate Similarity	NPD4589	Approved
0.7565	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7340	Approved
0.7542	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1791	Approved
0.7521	Intermediate Similarity	NPD1793	Approved
0.752	Intermediate Similarity	NPD5736	Approved
0.744	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2195	Approved
0.744	Intermediate Similarity	NPD2194	Approved
0.7436	Intermediate Similarity	NPD1398	Phase 1
0.7436	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD968	Approved
0.7417	Intermediate Similarity	NPD5303	Approved
0.7417	Intermediate Similarity	NPD7330	Discontinued
0.7417	Intermediate Similarity	NPD5304	Approved
0.7381	Intermediate Similarity	NPD3636	Approved
0.7381	Intermediate Similarity	NPD3635	Approved
0.7381	Intermediate Similarity	NPD3637	Approved
0.7377	Intermediate Similarity	NPD3026	Approved
0.7377	Intermediate Similarity	NPD3496	Discontinued
0.7377	Intermediate Similarity	NPD3023	Approved
0.7373	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3025	Approved
0.7355	Intermediate Similarity	NPD3024	Approved
0.7339	Intermediate Similarity	NPD4749	Approved
0.7323	Intermediate Similarity	NPD2605	Approved
0.7323	Intermediate Similarity	NPD2606	Approved
0.7317	Intermediate Similarity	NPD1201	Approved
0.7311	Intermediate Similarity	NPD709	Approved
0.7302	Intermediate Similarity	NPD4624	Approved
0.7297	Intermediate Similarity	NPD3028	Approved
0.7295	Intermediate Similarity	NPD4626	Approved
0.7295	Intermediate Similarity	NPD2286	Discontinued
0.7288	Intermediate Similarity	NPD5283	Phase 1
0.7287	Intermediate Similarity	NPD6663	Approved
0.7273	Intermediate Similarity	NPD9088	Approved
0.7266	Intermediate Similarity	NPD4625	Phase 3
0.7266	Intermediate Similarity	NPD5155	Approved
0.7266	Intermediate Similarity	NPD5156	Approved
0.7252	Intermediate Similarity	NPD4097	Suspended
0.725	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1755	Approved
0.7188	Intermediate Similarity	NPD3594	Approved
0.7188	Intermediate Similarity	NPD3595	Approved
0.7177	Intermediate Similarity	NPD1611	Approved
0.7168	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9500	Approved
0.7119	Intermediate Similarity	NPD228	Approved
0.7117	Intermediate Similarity	NPD9273	Approved
0.7107	Intermediate Similarity	NPD7636	Approved
0.7099	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6346	Approved
0.7099	Intermediate Similarity	NPD3620	Phase 2
0.7099	Intermediate Similarity	NPD2238	Phase 2
0.709	Intermediate Similarity	NPD6100	Approved
0.709	Intermediate Similarity	NPD6099	Approved
0.7087	Intermediate Similarity	NPD1470	Approved
0.7083	Intermediate Similarity	NPD9614	Approved
0.7083	Intermediate Similarity	NPD9618	Approved
0.7073	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5585	Approved
0.7063	Intermediate Similarity	NPD5327	Phase 3
0.7054	Intermediate Similarity	NPD4908	Phase 1
0.704	Intermediate Similarity	NPD1610	Phase 2
0.7025	Intermediate Similarity	NPD7157	Approved
0.7016	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2668	Approved
0.7016	Intermediate Similarity	NPD2667	Approved
0.7015	Intermediate Similarity	NPD7742	Approved
0.7015	Intermediate Similarity	NPD7743	Approved
0.6984	Remote Similarity	NPD2235	Phase 2
0.6984	Remote Similarity	NPD2231	Phase 2
0.697	Remote Similarity	NPD4140	Approved
0.6963	Remote Similarity	NPD2935	Discontinued
0.696	Remote Similarity	NPD3143	Discontinued
0.696	Remote Similarity	NPD1983	Approved
0.696	Remote Similarity	NPD1980	Approved
0.696	Remote Similarity	NPD1981	Approved
0.6957	Remote Similarity	NPD9610	Approved
0.6957	Remote Similarity	NPD9608	Approved
0.6953	Remote Similarity	NPD2797	Approved
0.6947	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5691	Approved
0.693	Remote Similarity	NPD4817	Approved
0.693	Remote Similarity	NPD4818	Approved
0.6917	Remote Similarity	NPD9379	Approved
0.6917	Remote Similarity	NPD9377	Approved
0.6917	Remote Similarity	NPD5735	Approved
0.6912	Remote Similarity	NPD4726	Approved
0.6912	Remote Similarity	NPD4725	Approved
0.6912	Remote Similarity	NPD4721	Approved
0.6911	Remote Similarity	NPD9616	Approved
0.6911	Remote Similarity	NPD9613	Approved
0.6911	Remote Similarity	NPD9615	Approved
0.6899	Remote Similarity	NPD6584	Phase 3
0.6889	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6387	Discontinued
0.688	Remote Similarity	NPD1778	Approved
0.6875	Remote Similarity	NPD1283	Approved
0.687	Remote Similarity	NPD7095	Approved
0.687	Remote Similarity	NPD3027	Phase 3
0.6869	Remote Similarity	NPD9087	Approved
0.6866	Remote Similarity	NPD6353	Approved
0.6864	Remote Similarity	NPD2684	Approved
0.6861	Remote Similarity	NPD4256	Phase 2
0.6861	Remote Similarity	NPD4257	Approved
0.6855	Remote Similarity	NPD316	Approved
0.6852	Remote Similarity	NPD9295	Approved
0.685	Remote Similarity	NPD1608	Approved
0.685	Remote Similarity	NPD3070	Discontinued
0.6846	Remote Similarity	NPD1712	Approved
0.6825	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3055	Approved
0.6822	Remote Similarity	NPD3053	Approved
0.6812	Remote Similarity	NPD3638	Discontinued
0.6809	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5451	Approved
0.6803	Remote Similarity	NPD475	Phase 2
0.6803	Remote Similarity	NPD2629	Approved
0.68	Remote Similarity	NPD1651	Approved
0.68	Remote Similarity	NPD3444	Approved
0.68	Remote Similarity	NPD3445	Approved
0.68	Remote Similarity	NPD3443	Approved
0.6797	Remote Similarity	NPD1669	Approved
0.6797	Remote Similarity	NPD4659	Approved
0.6797	Remote Similarity	NPD4359	Approved
0.6794	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD600	Approved
0.6794	Remote Similarity	NPD596	Approved
0.6788	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3300	Phase 2
0.678	Remote Similarity	NPD290	Approved
0.6777	Remote Similarity	NPD1138	Approved
0.6774	Remote Similarity	NPD7644	Approved
0.6769	Remote Similarity	NPD2798	Approved
0.6763	Remote Similarity	NPD8166	Discontinued
0.6761	Remote Similarity	NPD6090	Discontinued
0.675	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5310	Approved
0.6744	Remote Similarity	NPD5311	Approved
0.6724	Remote Similarity	NPD3680	Approved
0.6724	Remote Similarity	NPD4229	Approved
0.6724	Remote Similarity	NPD3682	Approved
0.6724	Remote Similarity	NPD4231	Approved
0.6721	Remote Similarity	NPD4869	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