NPASS Compound

Structure

NPC469636 OpenBabel07101718282D 28 29 0 0 1 0 0 0 0 0999 V2000 2.7084 -3.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9486 1.8858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3996 0.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9819 -0.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6549 0.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5442 1.8069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6782 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5442 0.8069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4524 -1.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3413 -2.3231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8122 1.8069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6782 0.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1228 -1.6099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4498 -0.6649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0476 -0.9989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5084 1.1862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3367 -2.2281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4904 0.9970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0279 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8122 0.8069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2141 0.3069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5801 0.8146 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9461 0.3069 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 -1.6461 2.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9461 -0.6931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0381 1.6006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0801 0.8069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 18 21 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 21 28 1 6 0 0 0 22 24 1 0 0 0 0 22 27 1 1 0 0 0 23 26 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	423.253
LogP:	5.337
LogD:	4.37
LogS:	-5.566
# Rotatable Bonds:	5
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	3.953
Fsp3:	0.5
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:	-4.609
MDCK Permeability:	1.773825533746276e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.683

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	98.20380401611328%
Volume Distribution (VD):	1.344
Pgp-substrate:	2.0021812915802%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.714
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.143
CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.558
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	4.508
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.609
Drug-inuced Liver Injury (DILI):	0.837
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.517
Skin Sensitization:	0.75
Carcinogencity:	0.091
Eye Corrosion:	0.008
Eye Irritation:	0.192
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC469636

Natural Product ID:	NPC469636
*Common Name:**	Lyciferin D
IUPAC Name:	[(1R,2Z,4S,9E)-4-acetyloxy-2,5,5,9-tetramethylcycloundeca-2,9-dien-1-yl] benzoate
Synonyms:	Lyciferin D
Standard InCHIKey:	WZEJCPHMOSKQHH-BFVMRLTISA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-17-10-9-15-24(4,5)22(27-19(3)25)16-18(2)21(14-13-17)28-23(26)20-11-7-6-8-12-20/h6-8,11-13,16,21-22H,9-10,14-15H2,1-5H3/b17-13+,18-16-/t21-,22+/m1/s1
SMILES:	CC(=O)O[C@H]1/C=C(/C)[C@@H](C/C=C(/CCCC1(C)C)C)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094940
PubChem CID:	46210896
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
NPO33092	ferula lycia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20329739]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[502070]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45000.0	nM	PMID[502070]

☑ 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 NPC469636 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	237
0.1-0.2	1094
0.2-0.3	2547
0.3-0.4	7394
0.4-0.5	11684
0.5-0.6	12865
0.6-0.7	5812
0.7-0.8	953
0.8-0.85	57
0.85-0.9	46
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9307	High Similarity	NPC474365
0.9307	High Similarity	NPC301943
0.91	High Similarity	NPC78701
0.91	High Similarity	NPC35448
0.901	High Similarity	NPC146351
0.901	High Similarity	NPC325497
0.9	High Similarity	NPC92754
0.9	High Similarity	NPC276775
0.9	High Similarity	NPC249912
0.8981	High Similarity	NPC307651
0.8972	High Similarity	NPC270699
0.8972	High Similarity	NPC82899
0.8962	High Similarity	NPC251854
0.8962	High Similarity	NPC93084
0.8929	High Similarity	NPC473243
0.8911	High Similarity	NPC225060
0.8889	High Similarity	NPC128368
0.8879	High Similarity	NPC1082
0.8879	High Similarity	NPC305912
0.8868	High Similarity	NPC83628
0.8868	High Similarity	NPC17417
0.8868	High Similarity	NPC474364
0.8868	High Similarity	NPC10251
0.8868	High Similarity	NPC265407
0.885	High Similarity	NPC50872
0.88	High Similarity	NPC130398
0.8785	High Similarity	NPC214067
0.8785	High Similarity	NPC196246
0.8774	High Similarity	NPC56493
0.8762	High Similarity	NPC269457
0.8738	High Similarity	NPC70624
0.8738	High Similarity	NPC42211
0.8704	High Similarity	NPC476003
0.8704	High Similarity	NPC474157
0.8679	High Similarity	NPC119271
0.8641	High Similarity	NPC118343
0.8641	High Similarity	NPC203925
0.8611	High Similarity	NPC174099
0.8559	High Similarity	NPC210092
0.8545	High Similarity	NPC161611
0.8532	High Similarity	NPC210089
0.8491	Intermediate Similarity	NPC31786
0.8476	Intermediate Similarity	NPC188895
0.8475	Intermediate Similarity	NPC275576
0.8475	Intermediate Similarity	NPC476599
0.8468	Intermediate Similarity	NPC153053
0.8468	Intermediate Similarity	NPC474363
0.8455	Intermediate Similarity	NPC321852
0.8411	Intermediate Similarity	NPC209632
0.8403	Intermediate Similarity	NPC204579
0.8403	Intermediate Similarity	NPC169913
0.8396	Intermediate Similarity	NPC89886
0.8378	Intermediate Similarity	NPC272524
0.8376	Intermediate Similarity	NPC472703
0.8364	Intermediate Similarity	NPC260818
0.8333	Intermediate Similarity	NPC30594
0.8333	Intermediate Similarity	NPC37622
0.8319	Intermediate Similarity	NPC149691
0.8318	Intermediate Similarity	NPC114594
0.8305	Intermediate Similarity	NPC472704
0.8304	Intermediate Similarity	NPC308744
0.83	Intermediate Similarity	NPC173443
0.8288	Intermediate Similarity	NPC474314
0.8288	Intermediate Similarity	NPC158282
0.825	Intermediate Similarity	NPC473220
0.825	Intermediate Similarity	NPC470753
0.825	Intermediate Similarity	NPC110211
0.825	Intermediate Similarity	NPC472706
0.8235	Intermediate Similarity	NPC295664
0.823	Intermediate Similarity	NPC474685
0.8224	Intermediate Similarity	NPC60679
0.8214	Intermediate Similarity	NPC474176
0.82	Intermediate Similarity	NPC304760
0.8198	Intermediate Similarity	NPC167504
0.8197	Intermediate Similarity	NPC147561
0.8197	Intermediate Similarity	NPC475508
0.8197	Intermediate Similarity	NPC272946
0.8197	Intermediate Similarity	NPC42234
0.819	Intermediate Similarity	NPC204784
0.8182	Intermediate Similarity	NPC85493
0.8182	Intermediate Similarity	NPC269023
0.8182	Intermediate Similarity	NPC99846
0.8182	Intermediate Similarity	NPC472707
0.8174	Intermediate Similarity	NPC469574
0.8167	Intermediate Similarity	NPC470765
0.8158	Intermediate Similarity	NPC226093
0.8142	Intermediate Similarity	NPC196075
0.8131	Intermediate Similarity	NPC45613
0.813	Intermediate Similarity	NPC470278
0.8125	Intermediate Similarity	NPC79496
0.8119	Intermediate Similarity	NPC220893
0.81	Intermediate Similarity	NPC89377
0.8095	Intermediate Similarity	NPC270654
0.8065	Intermediate Similarity	NPC477360
0.8065	Intermediate Similarity	NPC238370
0.8065	Intermediate Similarity	NPC233860
0.8065	Intermediate Similarity	NPC233692
0.8065	Intermediate Similarity	NPC239358
0.8065	Intermediate Similarity	NPC472394
0.8058	Intermediate Similarity	NPC77273
0.8056	Intermediate Similarity	NPC234305
0.8049	Intermediate Similarity	NPC473247
0.8	Intermediate Similarity	NPC477364
0.8	Intermediate Similarity	NPC472316
0.8	Intermediate Similarity	NPC474376
0.8	Intermediate Similarity	NPC100353
0.8	Intermediate Similarity	NPC475203
0.8	Intermediate Similarity	NPC472248
0.8	Intermediate Similarity	NPC472656
0.8	Intermediate Similarity	NPC318107
0.8	Intermediate Similarity	NPC472315
0.7982	Intermediate Similarity	NPC477411
0.7982	Intermediate Similarity	NPC85977
0.7981	Intermediate Similarity	NPC261181
0.7963	Intermediate Similarity	NPC25458
0.7961	Intermediate Similarity	NPC119631
0.7944	Intermediate Similarity	NPC217621
0.7944	Intermediate Similarity	NPC472318
0.7944	Intermediate Similarity	NPC98911
0.7937	Intermediate Similarity	NPC48929
0.7937	Intermediate Similarity	NPC203486
0.7937	Intermediate Similarity	NPC472250
0.7937	Intermediate Similarity	NPC311492
0.7937	Intermediate Similarity	NPC126516
0.7937	Intermediate Similarity	NPC324898
0.7937	Intermediate Similarity	NPC134937
0.7937	Intermediate Similarity	NPC298547
0.7937	Intermediate Similarity	NPC153617
0.7937	Intermediate Similarity	NPC28836
0.7937	Intermediate Similarity	NPC474608
0.7937	Intermediate Similarity	NPC477368
0.7937	Intermediate Similarity	NPC329913
0.7937	Intermediate Similarity	NPC477359
0.7934	Intermediate Similarity	NPC246166
0.7928	Intermediate Similarity	NPC249811
0.7917	Intermediate Similarity	NPC223351
0.7913	Intermediate Similarity	NPC474095
0.7913	Intermediate Similarity	NPC306740
0.79	Intermediate Similarity	NPC58616
0.79	Intermediate Similarity	NPC294134
0.7881	Intermediate Similarity	NPC472708
0.7874	Intermediate Similarity	NPC475262
0.7874	Intermediate Similarity	NPC200154
0.7874	Intermediate Similarity	NPC17877
0.7874	Intermediate Similarity	NPC265459
0.7874	Intermediate Similarity	NPC270364
0.7874	Intermediate Similarity	NPC149401
0.7874	Intermediate Similarity	NPC290833
0.7874	Intermediate Similarity	NPC477367
0.7874	Intermediate Similarity	NPC472247
0.7874	Intermediate Similarity	NPC473399
0.7874	Intermediate Similarity	NPC473216
0.7874	Intermediate Similarity	NPC195647
0.7874	Intermediate Similarity	NPC477896
0.7874	Intermediate Similarity	NPC66761
0.7874	Intermediate Similarity	NPC279637
0.7874	Intermediate Similarity	NPC232888
0.7874	Intermediate Similarity	NPC472577
0.7874	Intermediate Similarity	NPC79699
0.7874	Intermediate Similarity	NPC291638
0.7874	Intermediate Similarity	NPC477893
0.7869	Intermediate Similarity	NPC121272
0.7864	Intermediate Similarity	NPC213156
0.7864	Intermediate Similarity	NPC240108
0.7863	Intermediate Similarity	NPC45794
0.7857	Intermediate Similarity	NPC40178
0.7851	Intermediate Similarity	NPC471466
0.785	Intermediate Similarity	NPC229242
0.7845	Intermediate Similarity	NPC471616
0.784	Intermediate Similarity	NPC475478
0.784	Intermediate Similarity	NPC72915
0.7838	Intermediate Similarity	NPC136962
0.7812	Intermediate Similarity	NPC285221
0.7812	Intermediate Similarity	NPC472551
0.7812	Intermediate Similarity	NPC202729
0.7812	Intermediate Similarity	NPC52523
0.7812	Intermediate Similarity	NPC194769
0.7812	Intermediate Similarity	NPC472372
0.7812	Intermediate Similarity	NPC217673
0.7812	Intermediate Similarity	NPC472374
0.7812	Intermediate Similarity	NPC472545
0.7812	Intermediate Similarity	NPC477358
0.781	Intermediate Similarity	NPC23453
0.7807	Intermediate Similarity	NPC139946
0.7805	Intermediate Similarity	NPC51292
0.7798	Intermediate Similarity	NPC304873
0.7797	Intermediate Similarity	NPC293424
0.7787	Intermediate Similarity	NPC125053
0.7778	Intermediate Similarity	NPC15083
0.7778	Intermediate Similarity	NPC475569
0.7778	Intermediate Similarity	NPC190298
0.7768	Intermediate Similarity	NPC47536
0.7768	Intermediate Similarity	NPC20485
0.7767	Intermediate Similarity	NPC9822
0.776	Intermediate Similarity	NPC194979
0.776	Intermediate Similarity	NPC471832
0.7759	Intermediate Similarity	NPC228936
0.7757	Intermediate Similarity	NPC253423
0.7752	Intermediate Similarity	NPC86772
0.7752	Intermediate Similarity	NPC27721

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 NPC469636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	846
0.2-0.3	1267
0.3-0.4	2633
0.4-0.5	2420
0.5-0.6	1285
0.6-0.7	423
0.7-0.8	64
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9057	High Similarity	NPD2181	Clinical (unspecified phase)
0.8868	High Similarity	NPD2182	Approved
0.8641	High Similarity	NPD1238	Approved
0.8491	Intermediate Similarity	NPD164	Approved
0.8349	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD6287	Discontinued
0.8108	Intermediate Similarity	NPD2067	Discontinued
0.8	Intermediate Similarity	NPD9259	Approved
0.8	Intermediate Similarity	NPD9257	Approved
0.7981	Intermediate Similarity	NPD1202	Approved
0.7903	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7008	Discontinued
0.7759	Intermediate Similarity	NPD2629	Approved
0.7759	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6647	Phase 2
0.7692	Intermediate Similarity	NPD9258	Approved
0.7692	Intermediate Similarity	NPD9256	Approved
0.768	Intermediate Similarity	NPD6832	Phase 2
0.7667	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1989	Approved
0.7658	Intermediate Similarity	NPD1237	Approved
0.7652	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD9545	Approved
0.7642	Intermediate Similarity	NPD2198	Approved
0.7642	Intermediate Similarity	NPD2199	Approved
0.7634	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5951	Approved
0.7524	Intermediate Similarity	NPD3673	Approved
0.7524	Intermediate Similarity	NPD3672	Approved
0.7523	Intermediate Similarity	NPD9495	Approved
0.75	Intermediate Similarity	NPD7713	Phase 3
0.75	Intermediate Similarity	NPD5909	Discontinued
0.748	Intermediate Similarity	NPD3972	Approved
0.7479	Intermediate Similarity	NPD9493	Approved
0.7455	Intermediate Similarity	NPD2066	Phase 3
0.7411	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1930	Approved
0.7411	Intermediate Similarity	NPD1929	Approved
0.7407	Intermediate Similarity	NPD9260	Approved
0.7405	Intermediate Similarity	NPD2569	Approved
0.7405	Intermediate Similarity	NPD2567	Approved
0.7404	Intermediate Similarity	NPD1087	Approved
0.7395	Intermediate Similarity	NPD4198	Discontinued
0.7383	Intermediate Similarity	NPD1088	Approved
0.7381	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1241	Discontinued
0.7368	Intermediate Similarity	NPD3134	Approved
0.7353	Intermediate Similarity	NPD7236	Approved
0.7344	Intermediate Similarity	NPD6039	Approved
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7317	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1358	Approved
0.73	Intermediate Similarity	NPD9490	Approved
0.7297	Intermediate Similarity	NPD7798	Approved
0.7288	Intermediate Similarity	NPD7094	Approved
0.7288	Intermediate Similarity	NPD6858	Approved
0.7264	Intermediate Similarity	NPD800	Approved
0.7258	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1019	Discontinued
0.7238	Intermediate Similarity	NPD1282	Approved
0.7236	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5667	Approved
0.7207	Intermediate Similarity	NPD5926	Approved
0.72	Intermediate Similarity	NPD9717	Approved
0.7197	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1089	Approved
0.7196	Intermediate Similarity	NPD1086	Approved
0.7196	Intermediate Similarity	NPD1090	Approved
0.7184	Intermediate Similarity	NPD9491	Approved
0.7179	Intermediate Similarity	NPD4234	Approved
0.7179	Intermediate Similarity	NPD4233	Approved
0.7176	Intermediate Similarity	NPD3373	Approved
0.7143	Intermediate Similarity	NPD5277	Phase 2
0.7131	Intermediate Similarity	NPD2347	Approved
0.712	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6085	Phase 2
0.7105	Intermediate Similarity	NPD9261	Approved
0.7103	Intermediate Similarity	NPD5347	Phase 2
0.7103	Intermediate Similarity	NPD5346	Phase 2
0.7092	Intermediate Similarity	NPD7239	Suspended
0.7091	Intermediate Similarity	NPD1693	Approved
0.7083	Intermediate Similarity	NPD6010	Discontinued
0.7075	Intermediate Similarity	NPD4793	Discontinued
0.7063	Intermediate Similarity	NPD6637	Approved
0.7045	Intermediate Similarity	NPD4307	Phase 2
0.7034	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5235	Approved
0.7034	Intermediate Similarity	NPD5239	Approved
0.7034	Intermediate Similarity	NPD1756	Approved
0.7034	Intermediate Similarity	NPD5240	Approved
0.7034	Intermediate Similarity	NPD5237	Approved
0.7034	Intermediate Similarity	NPD1752	Approved
0.7034	Intermediate Similarity	NPD5236	Approved
0.7031	Intermediate Similarity	NPD9567	Approved
0.7031	Intermediate Similarity	NPD552	Approved
0.7031	Intermediate Similarity	NPD553	Approved
0.703	Intermediate Similarity	NPD227	Approved
0.703	Intermediate Similarity	NPD225	Approved
0.7029	Intermediate Similarity	NPD3887	Approved
0.7023	Intermediate Similarity	NPD2313	Discontinued
0.7023	Intermediate Similarity	NPD3764	Approved
0.7018	Intermediate Similarity	NPD1932	Approved
0.7016	Intermediate Similarity	NPD5585	Approved
0.7007	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2607	Approved
0.6992	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4806	Approved
0.6984	Remote Similarity	NPD4807	Approved
0.6983	Remote Similarity	NPD5048	Discontinued
0.6977	Remote Similarity	NPD2798	Approved
0.6975	Remote Similarity	NPD2201	Approved
0.6975	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7609	Phase 3
0.6963	Remote Similarity	NPD2799	Discontinued
0.696	Remote Similarity	NPD5305	Approved
0.696	Remote Similarity	NPD5306	Approved
0.6957	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1876	Approved
0.695	Remote Similarity	NPD6273	Approved
0.6935	Remote Similarity	NPD1894	Discontinued
0.693	Remote Similarity	NPD2550	Approved
0.693	Remote Similarity	NPD2553	Approved
0.693	Remote Similarity	NPD2555	Approved
0.693	Remote Similarity	NPD2549	Approved
0.693	Remote Similarity	NPD2552	Approved
0.693	Remote Similarity	NPD2558	Approved
0.6923	Remote Similarity	NPD6685	Approved
0.6917	Remote Similarity	NPD969	Suspended
0.6912	Remote Similarity	NPD2935	Discontinued
0.6909	Remote Similarity	NPD7631	Approved
0.6905	Remote Similarity	NPD3496	Discontinued
0.6905	Remote Similarity	NPD4136	Approved
0.6905	Remote Similarity	NPD4106	Approved
0.6905	Remote Similarity	NPD4135	Approved
0.6899	Remote Similarity	NPD3266	Approved
0.6899	Remote Similarity	NPD1203	Approved
0.6899	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD2797	Approved
0.6894	Remote Similarity	NPD6798	Discontinued
0.6891	Remote Similarity	NPD1317	Discontinued
0.6887	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4766	Approved
0.688	Remote Similarity	NPD5691	Approved
0.688	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5157	Phase 1
0.6875	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5159	Phase 2
0.687	Remote Similarity	NPD4188	Approved
0.687	Remote Similarity	NPD4189	Approved
0.6866	Remote Similarity	NPD6355	Discontinued
0.6866	Remote Similarity	NPD1933	Approved
0.6864	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9267	Approved
0.6864	Remote Similarity	NPD9263	Approved
0.6864	Remote Similarity	NPD9264	Approved
0.6861	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7611	Approved
0.686	Remote Similarity	NPD5535	Approved
0.6847	Remote Similarity	NPD1563	Approved
0.6838	Remote Similarity	NPD4308	Phase 3
0.6835	Remote Similarity	NPD8166	Discontinued
0.6835	Remote Similarity	NPD7003	Approved
0.6827	Remote Similarity	NPD942	Approved
0.6827	Remote Similarity	NPD226	Approved
0.6825	Remote Similarity	NPD1778	Approved
0.6825	Remote Similarity	NPD17	Approved
0.6818	Remote Similarity	NPD1239	Approved
0.6815	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3495	Discontinued
0.6812	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9266	Approved
0.6807	Remote Similarity	NPD74	Approved
0.6807	Remote Similarity	NPD2329	Discontinued
0.6806	Remote Similarity	NPD7458	Discontinued
0.6803	Remote Similarity	NPD2650	Approved
0.6803	Remote Similarity	NPD2652	Approved
0.6791	Remote Similarity	NPD3142	Approved
0.6791	Remote Similarity	NPD2979	Phase 3
0.6791	Remote Similarity	NPD3140	Approved
0.6788	Remote Similarity	NPD2796	Approved
0.678	Remote Similarity	NPD5704	Approved
0.678	Remote Similarity	NPD5705	Approved
0.678	Remote Similarity	NPD5706	Approved
0.6777	Remote Similarity	NPD9508	Approved
0.6774	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4574	Approved
0.6774	Remote Similarity	NPD4576	Approved
0.6772	Remote Similarity	NPD3847	Discontinued
0.6767	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3268	Approved
0.6765	Remote Similarity	NPD2670	Approved
0.6759	Remote Similarity	NPD6599	Discontinued
0.6752	Remote Similarity	NPD3047	Approved
0.6752	Remote Similarity	NPD3046	Approved
0.6752	Remote Similarity	NPD3048	Approved
0.6746	Remote Similarity	NPD4105	Approved
0.6746	Remote Similarity	NPD4102	Approved
0.6744	Remote Similarity	NPD4359	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