NPASS Compound

Structure

NPC73603 OpenBabel07101718222D 24 24 0 0 1 0 0 0 0 0999 V2000 5.1724 -1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5047 0.8455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4522 3.1462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7470 -2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2714 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6479 -1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7470 -2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4940 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6479 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7470 2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7532 2.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2714 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 -1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6784 1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 0.9749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7470 2.1906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6541 2.8399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1324 3.8793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4272 2.9237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 11 2 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 18 17 1 6 0 0 0 18 19 1 0 0 0 0 19 22 1 6 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	370.535
LogP:	1.797
LogD:	2.176
LogS:	-3.736
# Rotatable Bonds:	3
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	5.066
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.727
MDCK Permeability:	2.2086271201260388e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.56
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	83.3281478881836%
Volume Distribution (VD):	0.819
Pgp-substrate:	3.599778890609741%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	3.627
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.805
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.918
Carcinogencity:	0.606
Eye Corrosion:	0.013
Eye Irritation:	0.62
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC73603

Natural Product ID:	NPC73603
*Common Name:**	Crassumolide E
IUPAC Name:	(1S,2E,6E,9E,11R,14S)-11-hydroperoxy-14-(3-hydroxyprop-1-en-2-yl)-3,7,11-trimethylcyclotetradeca-2,6,9-trien-1-ol
Synonyms:	Crassumolide E
Standard InCHIKey:	HGPWGHBBMMTDTA-WWWHTDTNSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-15-7-5-8-16(2)13-19(22)18(17(3)14-21)10-12-20(4,24-23)11-6-9-15/h6-7,11,13,18-19,21-23H,3,5,8-10,12,14H2,1-2,4H3/b11-6+,15-7+,16-13+/t18-,19-,20-/m0/s1
SMILES:	C/C/1=CCC/C(=C/[C@@H]([C@@H](CC[C@](C)(/C=C/C1)OO)C(=C)CO)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL583706
PubChem CID:	25156700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000008] Cembrane 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
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	south china sea	n.a.	PMID[18512986]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973388]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548852]
NPO27251	Lobophytum crassum	Species	Alcyoniidae	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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[497486]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[497486]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[497486]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[497486]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[497486]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[497486]

☑ 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 NPC73603 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	169
0.1-0.2	1712
0.2-0.3	6674
0.3-0.4	17403
0.4-0.5	9626
0.5-0.6	5644
0.6-0.7	1299
0.7-0.8	146
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC226848
0.8571	High Similarity	NPC122239
0.8529	High Similarity	NPC304690
0.8529	High Similarity	NPC74722
0.8382	Intermediate Similarity	NPC305698
0.8333	Intermediate Similarity	NPC300593
0.8281	Intermediate Similarity	NPC475931
0.8235	Intermediate Similarity	NPC259299
0.8235	Intermediate Similarity	NPC163290
0.8209	Intermediate Similarity	NPC308844
0.8182	Intermediate Similarity	NPC473508
0.8154	Intermediate Similarity	NPC99487
0.8125	Intermediate Similarity	NPC181872
0.8088	Intermediate Similarity	NPC311736
0.8088	Intermediate Similarity	NPC267027
0.8	Intermediate Similarity	NPC329989
0.8	Intermediate Similarity	NPC239373
0.7973	Intermediate Similarity	NPC476703
0.7971	Intermediate Similarity	NPC82337
0.7887	Intermediate Similarity	NPC470041
0.7879	Intermediate Similarity	NPC66020
0.7867	Intermediate Similarity	NPC475980
0.7857	Intermediate Similarity	NPC224532
0.7846	Intermediate Similarity	NPC155025
0.7838	Intermediate Similarity	NPC268111
0.7838	Intermediate Similarity	NPC170148
0.7778	Intermediate Similarity	NPC477087
0.7778	Intermediate Similarity	NPC477086
0.7763	Intermediate Similarity	NPC476701
0.7761	Intermediate Similarity	NPC321867
0.7761	Intermediate Similarity	NPC207007
0.7761	Intermediate Similarity	NPC68679
0.7746	Intermediate Similarity	NPC472947
0.7733	Intermediate Similarity	NPC84360
0.7703	Intermediate Similarity	NPC60818
0.7703	Intermediate Similarity	NPC23231
0.7692	Intermediate Similarity	NPC477385
0.7692	Intermediate Similarity	NPC472465
0.7692	Intermediate Similarity	NPC52012
0.7692	Intermediate Similarity	NPC477390
0.7681	Intermediate Similarity	NPC471200
0.7671	Intermediate Similarity	NPC477085
0.7662	Intermediate Similarity	NPC96362
0.7656	Intermediate Similarity	NPC227135
0.7656	Intermediate Similarity	NPC281590
0.7656	Intermediate Similarity	NPC329686
0.7639	Intermediate Similarity	NPC4299
0.7632	Intermediate Similarity	NPC68119
0.7632	Intermediate Similarity	NPC137345
0.7632	Intermediate Similarity	NPC13823
0.7632	Intermediate Similarity	NPC181838
0.7619	Intermediate Similarity	NPC474496
0.7612	Intermediate Similarity	NPC240506
0.76	Intermediate Similarity	NPC236228
0.76	Intermediate Similarity	NPC256720
0.7568	Intermediate Similarity	NPC190859
0.7568	Intermediate Similarity	NPC306727
0.7564	Intermediate Similarity	NPC476646
0.7564	Intermediate Similarity	NPC112868
0.7538	Intermediate Similarity	NPC24443
0.7536	Intermediate Similarity	NPC309300
0.7531	Intermediate Similarity	NPC311163
0.75	Intermediate Similarity	NPC475251
0.75	Intermediate Similarity	NPC101622
0.75	Intermediate Similarity	NPC16964
0.75	Intermediate Similarity	NPC225342
0.75	Intermediate Similarity	NPC471560
0.7467	Intermediate Similarity	NPC32832
0.7465	Intermediate Similarity	NPC472253
0.7465	Intermediate Similarity	NPC472255
0.7465	Intermediate Similarity	NPC114651
0.7432	Intermediate Similarity	NPC329763
0.7432	Intermediate Similarity	NPC130665
0.7432	Intermediate Similarity	NPC476709
0.7429	Intermediate Similarity	NPC61503
0.7429	Intermediate Similarity	NPC19569
0.7419	Intermediate Similarity	NPC474460
0.7403	Intermediate Similarity	NPC477089
0.7397	Intermediate Similarity	NPC34834
0.7385	Intermediate Similarity	NPC148163
0.7385	Intermediate Similarity	NPC148216
0.7385	Intermediate Similarity	NPC130209
0.7368	Intermediate Similarity	NPC265588
0.7368	Intermediate Similarity	NPC310643
0.7368	Intermediate Similarity	NPC253190
0.7361	Intermediate Similarity	NPC471238
0.7353	Intermediate Similarity	NPC471081
0.7342	Intermediate Similarity	NPC471270
0.7342	Intermediate Similarity	NPC320525
0.7342	Intermediate Similarity	NPC249423
0.7333	Intermediate Similarity	NPC471525
0.7324	Intermediate Similarity	NPC202017
0.7324	Intermediate Similarity	NPC272125
0.7324	Intermediate Similarity	NPC326310
0.7317	Intermediate Similarity	NPC261266
0.7317	Intermediate Similarity	NPC477387
0.7317	Intermediate Similarity	NPC477389
0.7308	Intermediate Similarity	NPC86971
0.7302	Intermediate Similarity	NPC474495
0.7302	Intermediate Similarity	NPC473672
0.7297	Intermediate Similarity	NPC471662
0.7297	Intermediate Similarity	NPC471272
0.7297	Intermediate Similarity	NPC23954
0.7286	Intermediate Similarity	NPC110241
0.7284	Intermediate Similarity	NPC83702
0.7273	Intermediate Similarity	NPC91594
0.7273	Intermediate Similarity	NPC476439
0.7273	Intermediate Similarity	NPC476007
0.7273	Intermediate Similarity	NPC40049
0.7262	Intermediate Similarity	NPC115607
0.7262	Intermediate Similarity	NPC97103
0.7262	Intermediate Similarity	NPC128066
0.726	Intermediate Similarity	NPC217570
0.726	Intermediate Similarity	NPC90115
0.725	Intermediate Similarity	NPC50964
0.7229	Intermediate Similarity	NPC477388
0.7229	Intermediate Similarity	NPC477386
0.7229	Intermediate Similarity	NPC471056
0.7229	Intermediate Similarity	NPC471055
0.7222	Intermediate Similarity	NPC68703
0.7222	Intermediate Similarity	NPC69649
0.7222	Intermediate Similarity	NPC136813
0.7222	Intermediate Similarity	NPC477791
0.7215	Intermediate Similarity	NPC324772
0.7215	Intermediate Similarity	NPC236707
0.7215	Intermediate Similarity	NPC471266
0.7215	Intermediate Similarity	NPC95124
0.72	Intermediate Similarity	NPC265485
0.72	Intermediate Similarity	NPC220939
0.7195	Intermediate Similarity	NPC471494
0.7188	Intermediate Similarity	NPC40417
0.7188	Intermediate Similarity	NPC35756
0.7188	Intermediate Similarity	NPC294358
0.7183	Intermediate Similarity	NPC250836
0.7179	Intermediate Similarity	NPC83351
0.7179	Intermediate Similarity	NPC167891
0.7179	Intermediate Similarity	NPC121200
0.7176	Intermediate Similarity	NPC191323
0.7162	Intermediate Similarity	NPC471781
0.716	Intermediate Similarity	NPC320548
0.716	Intermediate Similarity	NPC69469
0.7143	Intermediate Similarity	NPC474668
0.7143	Intermediate Similarity	NPC474155
0.7143	Intermediate Similarity	NPC271070
0.7143	Intermediate Similarity	NPC26960
0.7143	Intermediate Similarity	NPC182102
0.7143	Intermediate Similarity	NPC83200
0.7143	Intermediate Similarity	NPC279200
0.7143	Intermediate Similarity	NPC473759
0.7143	Intermediate Similarity	NPC469880
0.7143	Intermediate Similarity	NPC126969
0.7143	Intermediate Similarity	NPC329773
0.7143	Intermediate Similarity	NPC131623
0.7125	Intermediate Similarity	NPC47761
0.7125	Intermediate Similarity	NPC474894
0.7125	Intermediate Similarity	NPC209620
0.7125	Intermediate Similarity	NPC315731
0.7125	Intermediate Similarity	NPC471661
0.7125	Intermediate Similarity	NPC23852
0.7125	Intermediate Similarity	NPC264245
0.7123	Intermediate Similarity	NPC167527
0.7123	Intermediate Similarity	NPC272961
0.7121	Intermediate Similarity	NPC232247
0.7121	Intermediate Similarity	NPC251666
0.7108	Intermediate Similarity	NPC6391
0.7108	Intermediate Similarity	NPC152808
0.7108	Intermediate Similarity	NPC476982
0.7108	Intermediate Similarity	NPC293287
0.7105	Intermediate Similarity	NPC471659
0.7105	Intermediate Similarity	NPC201048
0.7105	Intermediate Similarity	NPC476366
0.7093	Intermediate Similarity	NPC97404
0.7093	Intermediate Similarity	NPC41554
0.7089	Intermediate Similarity	NPC477088
0.7089	Intermediate Similarity	NPC139712
0.7089	Intermediate Similarity	NPC471537
0.7083	Intermediate Similarity	NPC476406
0.7073	Intermediate Similarity	NPC160517
0.7073	Intermediate Similarity	NPC205845
0.7073	Intermediate Similarity	NPC186155
0.7073	Intermediate Similarity	NPC78673
0.7073	Intermediate Similarity	NPC102048
0.7067	Intermediate Similarity	NPC477792
0.7067	Intermediate Similarity	NPC472254
0.7067	Intermediate Similarity	NPC477084
0.7067	Intermediate Similarity	NPC306085
0.7067	Intermediate Similarity	NPC242001
0.7067	Intermediate Similarity	NPC469343
0.7059	Intermediate Similarity	NPC23418
0.7059	Intermediate Similarity	NPC475830
0.7051	Intermediate Similarity	NPC470758
0.7051	Intermediate Similarity	NPC474826
0.7051	Intermediate Similarity	NPC281296
0.7051	Intermediate Similarity	NPC471061
0.7051	Intermediate Similarity	NPC470711
0.7051	Intermediate Similarity	NPC477427
0.7051	Intermediate Similarity	NPC471798
0.7051	Intermediate Similarity	NPC477426
0.7051	Intermediate Similarity	NPC31037
0.7051	Intermediate Similarity	NPC477425

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 NPC73603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	2303
0.2-0.3	3908
0.3-0.4	2058
0.4-0.5	552
0.5-0.6	114
0.6-0.7	53
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7761	Intermediate Similarity	NPD368	Approved
0.7385	Intermediate Similarity	NPD342	Phase 1
0.7284	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4820	Approved
0.7215	Intermediate Similarity	NPD4819	Approved
0.7215	Intermediate Similarity	NPD6931	Approved
0.7215	Intermediate Similarity	NPD6930	Phase 2
0.7215	Intermediate Similarity	NPD4822	Approved
0.7215	Intermediate Similarity	NPD7514	Phase 3
0.7215	Intermediate Similarity	NPD4821	Approved
0.7215	Intermediate Similarity	NPD7332	Phase 2
0.72	Intermediate Similarity	NPD4732	Discontinued
0.716	Intermediate Similarity	NPD6695	Phase 3
0.7089	Intermediate Similarity	NPD6929	Approved
0.7013	Intermediate Similarity	NPD8264	Approved
0.6962	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4268	Approved
0.6962	Remote Similarity	NPD4271	Approved
0.6962	Remote Similarity	NPD7145	Approved
0.6914	Remote Similarity	NPD6902	Approved
0.6883	Remote Similarity	NPD6924	Approved
0.6883	Remote Similarity	NPD6926	Approved
0.6835	Remote Similarity	NPD6932	Approved
0.6835	Remote Similarity	NPD6925	Approved
0.6835	Remote Similarity	NPD5776	Phase 2
0.6824	Remote Similarity	NPD7750	Discontinued
0.6824	Remote Similarity	NPD7524	Approved
0.679	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6893	Approved
0.6782	Remote Similarity	NPD7838	Discovery
0.6774	Remote Similarity	NPD4265	Approved
0.6747	Remote Similarity	NPD5332	Approved
0.6747	Remote Similarity	NPD5362	Discontinued
0.6747	Remote Similarity	NPD7154	Phase 3
0.6747	Remote Similarity	NPD5331	Approved
0.6709	Remote Similarity	NPD6933	Approved
0.6707	Remote Similarity	NPD4790	Discontinued
0.6707	Remote Similarity	NPD6898	Phase 1
0.6705	Remote Similarity	NPD7983	Approved
0.6629	Remote Similarity	NPD5779	Approved
0.6629	Remote Similarity	NPD5778	Approved
0.6628	Remote Similarity	NPD4251	Approved
0.6628	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4250	Approved
0.6627	Remote Similarity	NPD4270	Approved
0.6627	Remote Similarity	NPD4269	Approved
0.6585	Remote Similarity	NPD7509	Discontinued
0.6585	Remote Similarity	NPD7525	Registered
0.6543	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7087	Discontinued
0.6512	Remote Similarity	NPD4249	Approved
0.6494	Remote Similarity	NPD7143	Approved
0.6494	Remote Similarity	NPD7144	Approved
0.6489	Remote Similarity	NPD5344	Discontinued
0.6463	Remote Similarity	NPD6683	Phase 2
0.6452	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7150	Approved
0.641	Remote Similarity	NPD7152	Approved
0.641	Remote Similarity	NPD7151	Approved
0.6404	Remote Similarity	NPD46	Approved
0.6404	Remote Similarity	NPD6698	Approved
0.6395	Remote Similarity	NPD5363	Approved
0.6389	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4252	Approved
0.6375	Remote Similarity	NPD7339	Approved
0.6375	Remote Similarity	NPD6942	Approved
0.6364	Remote Similarity	NPD6923	Approved
0.6364	Remote Similarity	NPD6922	Approved
0.6333	Remote Similarity	NPD7637	Suspended
0.6322	Remote Similarity	NPD5786	Approved
0.631	Remote Similarity	NPD5369	Approved
0.6296	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4219	Approved
0.6237	Remote Similarity	NPD7839	Suspended
0.6222	Remote Similarity	NPD7136	Phase 2
0.6211	Remote Similarity	NPD6648	Approved
0.6207	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5368	Approved
0.6163	Remote Similarity	NPD6110	Phase 1
0.6071	Remote Similarity	NPD7645	Phase 2
0.6053	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4785	Approved
0.6049	Remote Similarity	NPD4784	Approved
0.6047	Remote Similarity	NPD6435	Approved
0.6044	Remote Similarity	NPD5785	Approved
0.6022	Remote Similarity	NPD5282	Discontinued
0.5974	Remote Similarity	NPD7331	Phase 2
0.5934	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5370	Suspended
0.5934	Remote Similarity	NPD6101	Approved
0.5922	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4786	Approved
0.5876	Remote Similarity	NPD7639	Approved
0.5876	Remote Similarity	NPD7640	Approved
0.587	Remote Similarity	NPD3168	Discontinued
0.5862	Remote Similarity	NPD3667	Approved
0.5844	Remote Similarity	NPD7341	Phase 2
0.5825	Remote Similarity	NPD6371	Approved
0.5814	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6411	Approved
0.5802	Remote Similarity	NPD4243	Approved
0.5789	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD3197	Phase 1
0.5686	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4748	Discontinued
0.5625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD4225	Approved
0.5604	Remote Similarity	NPD4519	Discontinued
0.5604	Remote Similarity	NPD4623	Approved
0.56	Remote Similarity	NPD5211	Phase 2

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