NPASS Compound

Structure

NPC474480 OpenBabel07101719142D 21 22 0 0 1 0 0 0 0 0999 V2000 1.2761 1.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3762 1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9523 1.3454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4725 -3.6797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7898 -1.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3317 -1.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1424 -0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9600 -2.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4805 0.7151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5355 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1466 -2.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2805 -2.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1538 -1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6620 -0.7495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2999 0.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4523 0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1454 -2.7347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9174 -0.3980 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8223 -1.3935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6762 0.7367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 19 5 1 1 0 0 0 20 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.136
LogD:	4.482
LogS:	-5.712
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	4.748
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.652
MDCK Permeability:	2.0862733435933478e-05
Pgp-inhibitor:	0.785
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.735
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652
Plasma Protein Binding (PPB):	93.03948211669922%
Volume Distribution (VD):	1.649
Pgp-substrate:	2.0485143661499023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.168
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.238
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.477
CYP2D6-inhibitor:	0.356
CYP2D6-substrate:	0.397
CYP3A4-inhibitor:	0.654
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	4.928
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.784
Skin Sensitization:	0.952
Carcinogencity:	0.047
Eye Corrosion:	0.187
Eye Irritation:	0.675
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC474480

Natural Product ID:	NPC474480
*Common Name:**	Edunol
IUPAC Name:	(1R,3aS,5E,9E,12aS)-3a,6,10-trimethyl-1-prop-1-en-2-yl-2,3,4,7,8,11,12,12a-octahydrocyclopenta[11]annulen-1-ol
Synonyms:	Edunol
Standard InCHIKey:	NUHPZDOCKJPIPC-UMFXKQKMSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-15(2)20(21)14-13-19(5)12-11-17(4)8-6-7-16(3)9-10-18(19)20/h7,11,18,21H,1,6,8-10,12-14H2,2-5H3/b16-7+,17-11+/t18-,19+,20-/m0/s1
SMILES:	C/C/1=CC[C@]2(C)CC[C@]([C@H]2CC/C(=C/CC1)/C)(O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469719
PubChem CID:	10039786
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22554	Eunicea laciniata	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7769391]
NPO22554	Eunicea laciniata	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[527773]

☑ 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 NPC474480 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	145
0.1-0.2	2322
0.2-0.3	15362
0.3-0.4	11959
0.4-0.5	7856
0.5-0.6	4009
0.6-0.7	924
0.7-0.8	99
0.8-0.85	9
0.85-0.9	6
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC252809
0.9167	High Similarity	NPC210346
0.9153	High Similarity	NPC5698
0.9	High Similarity	NPC323153
0.8788	High Similarity	NPC471660
0.873	High Similarity	NPC477009
0.873	High Similarity	NPC238352
0.8615	High Similarity	NPC224532
0.8571	High Similarity	NPC309300
0.8529	High Similarity	NPC471659
0.8525	High Similarity	NPC469321
0.8286	Intermediate Similarity	NPC310643
0.8254	Intermediate Similarity	NPC15152
0.8254	Intermediate Similarity	NPC63111
0.8197	Intermediate Similarity	NPC278550
0.8182	Intermediate Similarity	NPC136813
0.8154	Intermediate Similarity	NPC19569
0.8095	Intermediate Similarity	NPC135648
0.8028	Intermediate Similarity	NPC471658
0.8	Intermediate Similarity	NPC309178
0.7971	Intermediate Similarity	NPC471662
0.7937	Intermediate Similarity	NPC99480
0.7937	Intermediate Similarity	NPC184049
0.7931	Intermediate Similarity	NPC329773
0.791	Intermediate Similarity	NPC477791
0.7887	Intermediate Similarity	NPC251435
0.7879	Intermediate Similarity	NPC261782
0.7879	Intermediate Similarity	NPC205618
0.7879	Intermediate Similarity	NPC469326
0.7857	Intermediate Similarity	NPC14352
0.7857	Intermediate Similarity	NPC234527
0.7826	Intermediate Similarity	NPC475728
0.7794	Intermediate Similarity	NPC167527
0.7778	Intermediate Similarity	NPC126969
0.7761	Intermediate Similarity	NPC162309
0.7761	Intermediate Similarity	NPC279434
0.7733	Intermediate Similarity	NPC471661
0.7727	Intermediate Similarity	NPC287744
0.7727	Intermediate Similarity	NPC140233
0.7714	Intermediate Similarity	NPC41886
0.7681	Intermediate Similarity	NPC144647
0.7639	Intermediate Similarity	NPC313185
0.7632	Intermediate Similarity	NPC472465
0.7576	Intermediate Similarity	NPC279200
0.7568	Intermediate Similarity	NPC477514
0.7538	Intermediate Similarity	NPC162109
0.7538	Intermediate Similarity	NPC471081
0.7536	Intermediate Similarity	NPC160209
0.7534	Intermediate Similarity	NPC244488
0.7534	Intermediate Similarity	NPC247325
0.75	Intermediate Similarity	NPC329090
0.75	Intermediate Similarity	NPC27395
0.75	Intermediate Similarity	NPC472471
0.7429	Intermediate Similarity	NPC167272
0.7429	Intermediate Similarity	NPC22301
0.7429	Intermediate Similarity	NPC269877
0.7424	Intermediate Similarity	NPC274704
0.7424	Intermediate Similarity	NPC41160
0.7403	Intermediate Similarity	NPC256750
0.7403	Intermediate Similarity	NPC20262
0.7397	Intermediate Similarity	NPC77501
0.7397	Intermediate Similarity	NPC328104
0.7397	Intermediate Similarity	NPC319090
0.7397	Intermediate Similarity	NPC113639
0.7391	Intermediate Similarity	NPC472255
0.7391	Intermediate Similarity	NPC114651
0.7391	Intermediate Similarity	NPC472253
0.7385	Intermediate Similarity	NPC122239
0.7385	Intermediate Similarity	NPC52431
0.7385	Intermediate Similarity	NPC475931
0.7385	Intermediate Similarity	NPC310228
0.7377	Intermediate Similarity	NPC157781
0.7377	Intermediate Similarity	NPC306195
0.7377	Intermediate Similarity	NPC35519
0.7377	Intermediate Similarity	NPC181255
0.7377	Intermediate Similarity	NPC179169
0.7368	Intermediate Similarity	NPC324772
0.7368	Intermediate Similarity	NPC209944
0.7368	Intermediate Similarity	NPC241290
0.7368	Intermediate Similarity	NPC164840
0.7361	Intermediate Similarity	NPC474140
0.7333	Intermediate Similarity	NPC131623
0.7333	Intermediate Similarity	NPC477522
0.7333	Intermediate Similarity	NPC474216
0.7324	Intermediate Similarity	NPC471781
0.7324	Intermediate Similarity	NPC133873
0.7324	Intermediate Similarity	NPC49422
0.7324	Intermediate Similarity	NPC254845
0.7324	Intermediate Similarity	NPC9161
0.7313	Intermediate Similarity	NPC474155
0.7313	Intermediate Similarity	NPC81615
0.7313	Intermediate Similarity	NPC473759
0.7297	Intermediate Similarity	NPC476317
0.7297	Intermediate Similarity	NPC315261
0.7273	Intermediate Similarity	NPC264245
0.7273	Intermediate Similarity	NPC320525
0.7273	Intermediate Similarity	NPC47840
0.7273	Intermediate Similarity	NPC234264
0.726	Intermediate Similarity	NPC469534
0.726	Intermediate Similarity	NPC469533
0.726	Intermediate Similarity	NPC206875
0.726	Intermediate Similarity	NPC469593
0.7258	Intermediate Similarity	NPC192962
0.725	Intermediate Similarity	NPC152808
0.725	Intermediate Similarity	NPC293287
0.7246	Intermediate Similarity	NPC272125
0.7241	Intermediate Similarity	NPC49088
0.7237	Intermediate Similarity	NPC81306
0.7237	Intermediate Similarity	NPC30986
0.7237	Intermediate Similarity	NPC109546
0.7237	Intermediate Similarity	NPC28862
0.7237	Intermediate Similarity	NPC47982
0.7237	Intermediate Similarity	NPC209430
0.7237	Intermediate Similarity	NPC84694
0.7237	Intermediate Similarity	NPC1319
0.7237	Intermediate Similarity	NPC143182
0.7222	Intermediate Similarity	NPC164045
0.7213	Intermediate Similarity	NPC26906
0.7213	Intermediate Similarity	NPC214584
0.7206	Intermediate Similarity	NPC225415
0.7206	Intermediate Similarity	NPC290367
0.72	Intermediate Similarity	NPC476439
0.72	Intermediate Similarity	NPC198968
0.72	Intermediate Similarity	NPC155986
0.72	Intermediate Similarity	NPC318495
0.7188	Intermediate Similarity	NPC274396
0.7183	Intermediate Similarity	NPC90115
0.7183	Intermediate Similarity	NPC217570
0.7183	Intermediate Similarity	NPC474900
0.7179	Intermediate Similarity	NPC218616
0.7179	Intermediate Similarity	NPC296701
0.7179	Intermediate Similarity	NPC49964
0.7179	Intermediate Similarity	NPC87489
0.7164	Intermediate Similarity	NPC475251
0.7162	Intermediate Similarity	NPC230301
0.7162	Intermediate Similarity	NPC85831
0.7162	Intermediate Similarity	NPC304309
0.7162	Intermediate Similarity	NPC285893
0.7162	Intermediate Similarity	NPC22105
0.7162	Intermediate Similarity	NPC60818
0.7162	Intermediate Similarity	NPC134847
0.7162	Intermediate Similarity	NPC288035
0.7162	Intermediate Similarity	NPC215215
0.7162	Intermediate Similarity	NPC471723
0.7162	Intermediate Similarity	NPC136188
0.7162	Intermediate Similarity	NPC162742
0.7162	Intermediate Similarity	NPC23231
0.7162	Intermediate Similarity	NPC257347
0.7162	Intermediate Similarity	NPC28657
0.7162	Intermediate Similarity	NPC141071
0.7162	Intermediate Similarity	NPC265921
0.7143	Intermediate Similarity	NPC26117
0.7143	Intermediate Similarity	NPC69649
0.7143	Intermediate Similarity	NPC308522
0.7143	Intermediate Similarity	NPC68703
0.7143	Intermediate Similarity	NPC74885
0.7143	Intermediate Similarity	NPC234193
0.7143	Intermediate Similarity	NPC471656
0.7125	Intermediate Similarity	NPC318390
0.7123	Intermediate Similarity	NPC474743
0.7123	Intermediate Similarity	NPC469320
0.7123	Intermediate Similarity	NPC329763
0.7123	Intermediate Similarity	NPC300940
0.7123	Intermediate Similarity	NPC472506
0.7121	Intermediate Similarity	NPC309825
0.7119	Intermediate Similarity	NPC323445
0.7105	Intermediate Similarity	NPC285761
0.7105	Intermediate Similarity	NPC473943
0.7101	Intermediate Similarity	NPC187619
0.7101	Intermediate Similarity	NPC308844
0.7097	Intermediate Similarity	NPC68014
0.7089	Intermediate Similarity	NPC320548
0.7089	Intermediate Similarity	NPC475789
0.7089	Intermediate Similarity	NPC477667
0.7089	Intermediate Similarity	NPC472473
0.7089	Intermediate Similarity	NPC474634
0.7089	Intermediate Similarity	NPC310470
0.7083	Intermediate Similarity	NPC470041
0.7083	Intermediate Similarity	NPC34834
0.7073	Intermediate Similarity	NPC472677
0.7073	Intermediate Similarity	NPC58532
0.7067	Intermediate Similarity	NPC189883
0.7067	Intermediate Similarity	NPC240604
0.7067	Intermediate Similarity	NPC134330
0.7067	Intermediate Similarity	NPC237460
0.7067	Intermediate Similarity	NPC202642
0.7067	Intermediate Similarity	NPC472472
0.7067	Intermediate Similarity	NPC107059
0.7067	Intermediate Similarity	NPC129165
0.7067	Intermediate Similarity	NPC113733
0.7067	Intermediate Similarity	NPC96319
0.7067	Intermediate Similarity	NPC321381
0.7067	Intermediate Similarity	NPC300324
0.7067	Intermediate Similarity	NPC470362
0.7067	Intermediate Similarity	NPC469646
0.7067	Intermediate Similarity	NPC321016
0.7067	Intermediate Similarity	NPC46160
0.7059	Intermediate Similarity	NPC133368
0.7059	Intermediate Similarity	NPC124112
0.7059	Intermediate Similarity	NPC211291

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 NPC474480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	2873
0.2-0.3	4275
0.3-0.4	1289
0.4-0.5	288
0.5-0.6	177
0.6-0.7	87
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD4243	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.7639	Intermediate Similarity	NPD5275	Approved
0.7639	Intermediate Similarity	NPD4190	Phase 3
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.7429	Intermediate Similarity	NPD6922	Approved
0.7429	Intermediate Similarity	NPD6923	Approved
0.7368	Intermediate Similarity	NPD6930	Phase 2
0.7368	Intermediate Similarity	NPD6931	Approved
0.7324	Intermediate Similarity	NPD7144	Approved
0.7324	Intermediate Similarity	NPD7143	Approved
0.7297	Intermediate Similarity	NPD6933	Approved
0.7237	Intermediate Similarity	NPD4195	Approved
0.7237	Intermediate Similarity	NPD6929	Approved
0.7222	Intermediate Similarity	NPD7151	Approved
0.7222	Intermediate Similarity	NPD7152	Approved
0.7222	Intermediate Similarity	NPD7150	Approved
0.72	Intermediate Similarity	NPD5776	Phase 2
0.72	Intermediate Similarity	NPD6925	Approved
0.7162	Intermediate Similarity	NPD7339	Approved
0.7162	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD7514	Phase 3
0.7105	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7145	Approved
0.7089	Intermediate Similarity	NPD6695	Phase 3
0.7067	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6932	Approved
0.6962	Remote Similarity	NPD4223	Phase 3
0.6962	Remote Similarity	NPD4221	Approved
0.6951	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD7332	Phase 2
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD7525	Registered
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6914	Remote Similarity	NPD5329	Approved
0.6914	Remote Similarity	NPD6893	Approved
0.6883	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5331	Approved
0.6875	Remote Similarity	NPD5332	Approved
0.6875	Remote Similarity	NPD5362	Discontinued
0.6835	Remote Similarity	NPD6902	Approved
0.6835	Remote Similarity	NPD6898	Phase 1
0.6835	Remote Similarity	NPD4790	Discontinued
0.6795	Remote Similarity	NPD6683	Phase 2
0.679	Remote Similarity	NPD4197	Approved
0.6747	Remote Similarity	NPD7750	Discontinued
0.6747	Remote Similarity	NPD7524	Approved
0.6709	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6627	Remote Similarity	NPD4689	Approved
0.6627	Remote Similarity	NPD5205	Approved
0.6627	Remote Similarity	NPD4693	Phase 3
0.6627	Remote Similarity	NPD4690	Approved
0.6627	Remote Similarity	NPD5690	Phase 2
0.6627	Remote Similarity	NPD5280	Approved
0.6627	Remote Similarity	NPD4688	Approved
0.6627	Remote Similarity	NPD4138	Approved
0.6627	Remote Similarity	NPD4694	Approved
0.6543	Remote Similarity	NPD4269	Approved
0.6543	Remote Similarity	NPD4270	Approved
0.6515	Remote Similarity	NPD342	Phase 1
0.6506	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4748	Discontinued
0.6494	Remote Similarity	NPD8264	Approved
0.6471	Remote Similarity	NPD4518	Approved
0.6471	Remote Similarity	NPD4722	Approved
0.6471	Remote Similarity	NPD4723	Approved
0.6437	Remote Similarity	NPD7087	Discontinued
0.642	Remote Similarity	NPD5369	Approved
0.642	Remote Similarity	NPD4692	Approved
0.642	Remote Similarity	NPD4139	Approved
0.6395	Remote Similarity	NPD4753	Phase 2
0.6386	Remote Similarity	NPD3666	Approved
0.6386	Remote Similarity	NPD4786	Approved
0.6386	Remote Similarity	NPD3665	Phase 1
0.6386	Remote Similarity	NPD3133	Approved
0.6322	Remote Similarity	NPD5785	Approved
0.6322	Remote Similarity	NPD4096	Approved
0.6322	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5363	Approved
0.6301	Remote Similarity	NPD7331	Phase 2
0.6296	Remote Similarity	NPD4252	Approved
0.6296	Remote Similarity	NPD5368	Approved
0.6265	Remote Similarity	NPD4788	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6235	Remote Similarity	NPD6098	Approved
0.6235	Remote Similarity	NPD5786	Approved
0.6207	Remote Similarity	NPD6051	Approved
0.618	Remote Similarity	NPD4202	Approved
0.6176	Remote Similarity	NPD4219	Approved
0.6145	Remote Similarity	NPD6435	Approved
0.6145	Remote Similarity	NPD3667	Approved
0.6087	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD7154	Phase 3
0.6067	Remote Similarity	NPD7637	Suspended
0.6047	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4623	Approved
0.6047	Remote Similarity	NPD5279	Phase 3
0.6047	Remote Similarity	NPD4519	Discontinued
0.6044	Remote Similarity	NPD5695	Phase 3
0.6044	Remote Similarity	NPD5210	Approved
0.6044	Remote Similarity	NPD4629	Approved
0.6023	Remote Similarity	NPD6904	Approved
0.6023	Remote Similarity	NPD6080	Approved
0.6023	Remote Similarity	NPD5328	Approved
0.6023	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD5133	Approved
0.6	Remote Similarity	NPD1346	Approved
0.5977	Remote Similarity	NPD4251	Approved
0.5977	Remote Similarity	NPD4250	Approved
0.5976	Remote Similarity	NPD7645	Phase 2
0.5955	Remote Similarity	NPD7136	Phase 2
0.5946	Remote Similarity	NPD7341	Phase 2
0.5914	Remote Similarity	NPD4755	Approved
0.5909	Remote Similarity	NPD5208	Approved
0.5889	Remote Similarity	NPD5693	Phase 1
0.5889	Remote Similarity	NPD6050	Approved
0.5889	Remote Similarity	NPD6079	Approved
0.5876	Remote Similarity	NPD5141	Approved
0.5873	Remote Similarity	NPD4265	Approved
0.5862	Remote Similarity	NPD5330	Approved
0.5862	Remote Similarity	NPD6684	Approved
0.5862	Remote Similarity	NPD4249	Approved
0.5862	Remote Similarity	NPD7334	Approved
0.5862	Remote Similarity	NPD3618	Phase 1
0.5862	Remote Similarity	NPD7146	Approved
0.5862	Remote Similarity	NPD7521	Approved
0.5862	Remote Similarity	NPD6409	Approved
0.5854	Remote Similarity	NPD3617	Approved
0.5851	Remote Similarity	NPD5696	Approved
0.5824	Remote Similarity	NPD6399	Phase 3
0.5823	Remote Similarity	NPD4732	Discontinued
0.5814	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5285	Approved
0.5789	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD5286	Approved
0.5789	Remote Similarity	NPD4700	Approved
0.5789	Remote Similarity	NPD7640	Approved
0.5789	Remote Similarity	NPD4696	Approved
0.5778	Remote Similarity	NPD5207	Approved
0.5778	Remote Similarity	NPD5692	Phase 3
0.5769	Remote Similarity	NPD4747	Approved
0.5761	Remote Similarity	NPD5707	Approved
0.5753	Remote Similarity	NPD4194	Approved
0.5753	Remote Similarity	NPD4192	Approved
0.5753	Remote Similarity	NPD4193	Approved
0.5753	Remote Similarity	NPD4191	Approved
0.575	Remote Similarity	NPD5733	Approved
0.573	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6903	Approved
0.5729	Remote Similarity	NPD5223	Approved
0.5714	Remote Similarity	NPD4695	Discontinued
0.5714	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5694	Approved
0.5699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD5276	Approved
0.5684	Remote Similarity	NPD7638	Approved
0.567	Remote Similarity	NPD5224	Approved
0.567	Remote Similarity	NPD5226	Approved
0.567	Remote Similarity	NPD5091	Approved
0.567	Remote Similarity	NPD4633	Approved
0.567	Remote Similarity	NPD5225	Approved
0.5657	Remote Similarity	NPD6402	Approved
0.5657	Remote Similarity	NPD7128	Approved
0.5657	Remote Similarity	NPD6675	Approved
0.5657	Remote Similarity	NPD5739	Approved
0.5647	Remote Similarity	NPD857	Phase 3
0.5641	Remote Similarity	NPD15	Approved
0.5641	Remote Similarity	NPD1082	Approved
0.5641	Remote Similarity	NPD791	Approved
0.5641	Remote Similarity	NPD4137	Phase 3
0.5632	Remote Similarity	NPD3668	Phase 3
0.5625	Remote Similarity	NPD6404	Discontinued
0.5612	Remote Similarity	NPD5175	Approved
0.5612	Remote Similarity	NPD4754	Approved
0.5612	Remote Similarity	NPD5174	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