NPASS Compound

Structure

CID221421 OpenBabel06191716012D 34 39 0 0 1 0 0 0 0 0999 V2000 5.3254 0.7570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4555 1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9622 0.5716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0217 1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8669 -1.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6470 0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8232 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6462 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6475 2.8517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8240 2.3769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8229 -0.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8241 -1.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6478 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2952 -1.9005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4716 -2.3757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0211 -0.1804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1175 -1.4248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6464 0.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4704 2.3759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1172 -0.4743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4711 -0.4748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5800 -0.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4699 1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8238 -0.4753 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 2.4714 -1.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4169 -2.4748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3243 2.8682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5656 -0.9489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0215 -1.7182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 1 0 0 0 19 15 1 6 0 0 0 19 23 1 0 0 0 0 19 34 1 0 0 0 0 20 26 1 0 0 0 0 20 27 1 1 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 23 17 1 6 0 0 0 23 24 1 0 0 0 0 24 30 1 6 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	503.349
LogP:	3.688
LogD:	4.302
LogS:	-4.565
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	5.095
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.262
MDCK Permeability:	6.0827176639577374e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	91.06205749511719%
Volume Distribution (VD):	0.878
Pgp-substrate:	2.1877732276916504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.43
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.33
CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.574

ADMET: Excretion

Clearance (CL):	4.563
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.326
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.516
Carcinogencity:	0.027
Eye Corrosion:	0.104
Eye Irritation:	0.25
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC221421

Natural Product ID:	NPC221421
*Common Name:**	Ochraceolide E
IUPAC Name:	n.a.
Synonyms:	ochraceolide E
Standard InCHIKey:	FOKMPXXMXCCMNO-FDZGXQMLSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-17-23-19(34-25(17)33)15-30(16-31)14-13-28(5)18(24(23)30)7-8-21-27(4)11-10-22(32)26(2,3)20(27)9-12-29(21,28)6/h18-21,23-24,31H,1,7-16H2,2-6H3/t18-,19+,20-,21+,23+,24+,27-,28+,29+,30-/m0/s1
SMILES:	C=C1[C@@H]2[C@@H](C[C@@]3(CC[C@]4(C)[C@@H](CC[C@@H]5[C@@]6(C)CCC(=O)C(C)(C)[C@@H]6CC[C@@]45C)[C@H]23)CO)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462966
PubChem CID:	44584469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800637]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158155]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277307]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28378	Kokoona ochracea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28378	Kokoona ochracea	Species	Celastraceae	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
ED50	13

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	12.2	ug ml-1	PMID[485027]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[485027]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	11.9	ug ml-1	PMID[485027]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[485027]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[485027]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[485027]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[485027]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[485027]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	18.8	ug ml-1	PMID[485027]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[485027]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.6	ug ml-1	PMID[485027]

☑ 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 NPC221421 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	241
0.1-0.2	1638
0.2-0.3	5823
0.3-0.4	13135
0.4-0.5	7845
0.5-0.6	6029
0.6-0.7	6030
0.7-0.8	1890
0.8-0.85	61
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC280877
0.9053	High Similarity	NPC475700
0.8544	High Similarity	NPC310586
0.8529	High Similarity	NPC170615
0.8529	High Similarity	NPC15396
0.8421	Intermediate Similarity	NPC472505
0.8416	Intermediate Similarity	NPC78427
0.8416	Intermediate Similarity	NPC16911
0.8411	Intermediate Similarity	NPC470311
0.84	Intermediate Similarity	NPC200054
0.84	Intermediate Similarity	NPC29410
0.8333	Intermediate Similarity	NPC108371
0.8333	Intermediate Similarity	NPC287676
0.83	Intermediate Similarity	NPC157686
0.83	Intermediate Similarity	NPC259042
0.83	Intermediate Similarity	NPC98639
0.8286	Intermediate Similarity	NPC28791
0.8286	Intermediate Similarity	NPC295366
0.8283	Intermediate Similarity	NPC199543
0.8269	Intermediate Similarity	NPC140723
0.8269	Intermediate Similarity	NPC87927
0.8265	Intermediate Similarity	NPC297474
0.8265	Intermediate Similarity	NPC54065
0.8252	Intermediate Similarity	NPC474327
0.8252	Intermediate Similarity	NPC253886
0.8252	Intermediate Similarity	NPC289148
0.8252	Intermediate Similarity	NPC163963
0.8252	Intermediate Similarity	NPC52899
0.8252	Intermediate Similarity	NPC121218
0.8235	Intermediate Similarity	NPC473155
0.8235	Intermediate Similarity	NPC38471
0.8235	Intermediate Similarity	NPC98837
0.8235	Intermediate Similarity	NPC162459
0.8235	Intermediate Similarity	NPC471038
0.8235	Intermediate Similarity	NPC20479
0.8235	Intermediate Similarity	NPC28864
0.8235	Intermediate Similarity	NPC38296
0.8208	Intermediate Similarity	NPC86852
0.8208	Intermediate Similarity	NPC251824
0.82	Intermediate Similarity	NPC469596
0.82	Intermediate Similarity	NPC225474
0.82	Intermediate Similarity	NPC148000
0.82	Intermediate Similarity	NPC47853
0.8182	Intermediate Similarity	NPC57304
0.8182	Intermediate Similarity	NPC293001
0.8182	Intermediate Similarity	NPC29821
0.8182	Intermediate Similarity	NPC171360
0.8182	Intermediate Similarity	NPC35959
0.8182	Intermediate Similarity	NPC133888
0.8182	Intermediate Similarity	NPC63193
0.8173	Intermediate Similarity	NPC88203
0.8173	Intermediate Similarity	NPC76866
0.8173	Intermediate Similarity	NPC148628
0.8173	Intermediate Similarity	NPC246736
0.8173	Intermediate Similarity	NPC286519
0.8173	Intermediate Similarity	NPC304832
0.8173	Intermediate Similarity	NPC214946
0.8163	Intermediate Similarity	NPC116620
0.8163	Intermediate Similarity	NPC155935
0.8155	Intermediate Similarity	NPC218383
0.8155	Intermediate Similarity	NPC293866
0.8155	Intermediate Similarity	NPC267921
0.8137	Intermediate Similarity	NPC475894
0.8137	Intermediate Similarity	NPC473963
0.8137	Intermediate Similarity	NPC253586
0.8131	Intermediate Similarity	NPC211224
0.8131	Intermediate Similarity	NPC189075
0.8131	Intermediate Similarity	NPC275539
0.8119	Intermediate Similarity	NPC210214
0.8113	Intermediate Similarity	NPC37600
0.8113	Intermediate Similarity	NPC278628
0.8113	Intermediate Similarity	NPC470309
0.8113	Intermediate Similarity	NPC231530
0.8105	Intermediate Similarity	NPC170862
0.8105	Intermediate Similarity	NPC245866
0.81	Intermediate Similarity	NPC244356
0.81	Intermediate Similarity	NPC224060
0.8095	Intermediate Similarity	NPC474775
0.8095	Intermediate Similarity	NPC36688
0.8081	Intermediate Similarity	NPC35809
0.8077	Intermediate Similarity	NPC46848
0.8077	Intermediate Similarity	NPC39683
0.8077	Intermediate Similarity	NPC252614
0.8073	Intermediate Similarity	NPC94650
0.8073	Intermediate Similarity	NPC470281
0.8061	Intermediate Similarity	NPC474719
0.8058	Intermediate Similarity	NPC89099
0.8058	Intermediate Similarity	NPC153792
0.8058	Intermediate Similarity	NPC271387
0.8041	Intermediate Similarity	NPC56593
0.8041	Intermediate Similarity	NPC185638
0.8041	Intermediate Similarity	NPC80590
0.8041	Intermediate Similarity	NPC85698
0.8039	Intermediate Similarity	NPC91771
0.8039	Intermediate Similarity	NPC473964
0.8039	Intermediate Similarity	NPC142529
0.8039	Intermediate Similarity	NPC93245
0.8039	Intermediate Similarity	NPC329910
0.8037	Intermediate Similarity	NPC110496
0.8021	Intermediate Similarity	NPC263974
0.802	Intermediate Similarity	NPC100257
0.802	Intermediate Similarity	NPC24861
0.802	Intermediate Similarity	NPC3359
0.802	Intermediate Similarity	NPC224410
0.8019	Intermediate Similarity	NPC13149
0.8019	Intermediate Similarity	NPC98603
0.8019	Intermediate Similarity	NPC47281
0.8018	Intermediate Similarity	NPC471398
0.8018	Intermediate Similarity	NPC123117
0.8018	Intermediate Similarity	NPC474181
0.8	Intermediate Similarity	NPC471747
0.8	Intermediate Similarity	NPC275990
0.8	Intermediate Similarity	NPC154101
0.8	Intermediate Similarity	NPC476964
0.8	Intermediate Similarity	NPC160506
0.8	Intermediate Similarity	NPC236217
0.8	Intermediate Similarity	NPC130840
0.7982	Intermediate Similarity	NPC179642
0.7982	Intermediate Similarity	NPC197428
0.7981	Intermediate Similarity	NPC476303
0.7981	Intermediate Similarity	NPC47024
0.798	Intermediate Similarity	NPC215556
0.7965	Intermediate Similarity	NPC475913
0.7963	Intermediate Similarity	NPC112895
0.7963	Intermediate Similarity	NPC218123
0.7963	Intermediate Similarity	NPC255082
0.7963	Intermediate Similarity	NPC94529
0.7963	Intermediate Similarity	NPC61411
0.7963	Intermediate Similarity	NPC231278
0.7961	Intermediate Similarity	NPC10864
0.7959	Intermediate Similarity	NPC134197
0.7959	Intermediate Similarity	NPC175293
0.7959	Intermediate Similarity	NPC33768
0.7959	Intermediate Similarity	NPC305029
0.7944	Intermediate Similarity	NPC50535
0.7944	Intermediate Similarity	NPC96377
0.7941	Intermediate Similarity	NPC470229
0.7941	Intermediate Similarity	NPC471624
0.7941	Intermediate Similarity	NPC469599
0.7941	Intermediate Similarity	NPC197158
0.7941	Intermediate Similarity	NPC470232
0.7938	Intermediate Similarity	NPC201655
0.7925	Intermediate Similarity	NPC470310
0.7925	Intermediate Similarity	NPC209298
0.7925	Intermediate Similarity	NPC139347
0.7925	Intermediate Similarity	NPC277074
0.7925	Intermediate Similarity	NPC122811
0.7925	Intermediate Similarity	NPC476237
0.7925	Intermediate Similarity	NPC469985
0.7925	Intermediate Similarity	NPC216114
0.7921	Intermediate Similarity	NPC200237
0.7921	Intermediate Similarity	NPC291373
0.7921	Intermediate Similarity	NPC294263
0.7917	Intermediate Similarity	NPC472740
0.7909	Intermediate Similarity	NPC231589
0.7909	Intermediate Similarity	NPC329953
0.7909	Intermediate Similarity	NPC214797
0.7909	Intermediate Similarity	NPC118860
0.7909	Intermediate Similarity	NPC471251
0.7905	Intermediate Similarity	NPC295276
0.79	Intermediate Similarity	NPC216284
0.79	Intermediate Similarity	NPC475776
0.7895	Intermediate Similarity	NPC475834
0.7895	Intermediate Similarity	NPC475041
0.7895	Intermediate Similarity	NPC474179
0.789	Intermediate Similarity	NPC241927
0.789	Intermediate Similarity	NPC471250
0.789	Intermediate Similarity	NPC258543
0.7885	Intermediate Similarity	NPC476807
0.7885	Intermediate Similarity	NPC476806
0.7885	Intermediate Similarity	NPC474793
0.7879	Intermediate Similarity	NPC229407
0.7879	Intermediate Similarity	NPC183374
0.7879	Intermediate Similarity	NPC16377
0.7879	Intermediate Similarity	NPC217983
0.7879	Intermediate Similarity	NPC254572
0.7879	Intermediate Similarity	NPC4309
0.7879	Intermediate Similarity	NPC211162
0.7879	Intermediate Similarity	NPC79549
0.7879	Intermediate Similarity	NPC48824
0.7879	Intermediate Similarity	NPC207114
0.7879	Intermediate Similarity	NPC250687
0.7864	Intermediate Similarity	NPC42042
0.7864	Intermediate Similarity	NPC13949
0.7864	Intermediate Similarity	NPC24956
0.7864	Intermediate Similarity	NPC284518
0.7864	Intermediate Similarity	NPC18019
0.7857	Intermediate Similarity	NPC12774
0.7857	Intermediate Similarity	NPC2783
0.7857	Intermediate Similarity	NPC70661
0.785	Intermediate Similarity	NPC301787
0.785	Intermediate Similarity	NPC202793
0.785	Intermediate Similarity	NPC96268
0.785	Intermediate Similarity	NPC84928
0.785	Intermediate Similarity	NPC255309
0.785	Intermediate Similarity	NPC474558
0.785	Intermediate Similarity	NPC29705
0.7843	Intermediate Similarity	NPC470385
0.7843	Intermediate Similarity	NPC473331
0.7843	Intermediate Similarity	NPC277399

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 NPC221421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	1956
0.2-0.3	4056
0.3-0.4	1999
0.4-0.5	448
0.5-0.6	197
0.6-0.7	221
0.7-0.8	39
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
0.8	Intermediate Similarity	NPD8034	Phase 2
0.8	Intermediate Similarity	NPD8035	Phase 2
0.7885	Intermediate Similarity	NPD7638	Approved
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.7755	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6399	Phase 3
0.7732	Intermediate Similarity	NPD4788	Approved
0.7615	Intermediate Similarity	NPD6008	Approved
0.7525	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8133	Approved
0.7453	Intermediate Similarity	NPD6083	Phase 2
0.7453	Intermediate Similarity	NPD6084	Phase 2
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD6053	Discontinued
0.7355	Intermediate Similarity	NPD7507	Approved
0.7353	Intermediate Similarity	NPD6903	Approved
0.7339	Intermediate Similarity	NPD7632	Discontinued
0.7327	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6684	Approved
0.7327	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD7521	Approved
0.7327	Intermediate Similarity	NPD7334	Approved
0.7327	Intermediate Similarity	NPD5330	Approved
0.7321	Intermediate Similarity	NPD7320	Approved
0.7321	Intermediate Similarity	NPD6899	Approved
0.7321	Intermediate Similarity	NPD6881	Approved
0.7297	Intermediate Similarity	NPD5739	Approved
0.7297	Intermediate Similarity	NPD6675	Approved
0.7297	Intermediate Similarity	NPD6402	Approved
0.7297	Intermediate Similarity	NPD7128	Approved
0.729	Intermediate Similarity	NPD7902	Approved
0.7281	Intermediate Similarity	NPD6650	Approved
0.7281	Intermediate Similarity	NPD6649	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7264	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.7236	Intermediate Similarity	NPD7736	Approved
0.7232	Intermediate Similarity	NPD5697	Approved
0.7222	Intermediate Similarity	NPD5696	Approved
0.7193	Intermediate Similarity	NPD7290	Approved
0.7193	Intermediate Similarity	NPD7102	Approved
0.7193	Intermediate Similarity	NPD6883	Approved
0.7177	Intermediate Similarity	NPD7319	Approved
0.717	Intermediate Similarity	NPD7748	Approved
0.7168	Intermediate Similarity	NPD6686	Approved
0.7168	Intermediate Similarity	NPD6011	Approved
0.7155	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7131	Intermediate Similarity	NPD7492	Approved
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6847	Approved
0.7129	Intermediate Similarity	NPD3666	Approved
0.7129	Intermediate Similarity	NPD3133	Approved
0.7129	Intermediate Similarity	NPD4786	Approved
0.7129	Intermediate Similarity	NPD3665	Phase 1
0.7105	Intermediate Similarity	NPD6013	Approved
0.7105	Intermediate Similarity	NPD6014	Approved
0.7105	Intermediate Similarity	NPD6012	Approved
0.7103	Intermediate Similarity	NPD5695	Phase 3
0.7083	Intermediate Similarity	NPD6054	Approved
0.708	Intermediate Similarity	NPD5701	Approved
0.7073	Intermediate Similarity	NPD6616	Approved
0.7069	Intermediate Similarity	NPD8297	Approved
0.7069	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD7327	Approved
0.7048	Intermediate Similarity	NPD5785	Approved
0.7041	Intermediate Similarity	NPD6697	Approved
0.7041	Intermediate Similarity	NPD6118	Approved
0.7041	Intermediate Similarity	NPD6114	Approved
0.7041	Intermediate Similarity	NPD6115	Approved
0.7025	Intermediate Similarity	NPD8033	Approved
0.7019	Intermediate Similarity	NPD5737	Approved
0.7019	Intermediate Similarity	NPD6672	Approved
0.7016	Intermediate Similarity	NPD7078	Approved
0.7009	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD7516	Approved
0.6983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5284	Approved
0.6981	Remote Similarity	NPD5281	Approved
0.6975	Remote Similarity	NPD6009	Approved
0.6967	Remote Similarity	NPD6370	Approved
0.6952	Remote Similarity	NPD4753	Phase 2
0.6952	Remote Similarity	NPD6904	Approved
0.6952	Remote Similarity	NPD6673	Approved
0.6952	Remote Similarity	NPD6080	Approved
0.6947	Remote Similarity	NPD5777	Approved
0.6944	Remote Similarity	NPD5210	Approved
0.6944	Remote Similarity	NPD4629	Approved
0.6942	Remote Similarity	NPD8294	Approved
0.6942	Remote Similarity	NPD6319	Approved
0.6942	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD8377	Approved
0.6939	Remote Similarity	NPD6116	Phase 1
0.6931	Remote Similarity	NPD3667	Approved
0.6916	Remote Similarity	NPD4202	Approved
0.6911	Remote Similarity	NPD7604	Phase 2
0.6897	Remote Similarity	NPD6371	Approved
0.6887	Remote Similarity	NPD5207	Approved
0.6885	Remote Similarity	NPD5983	Phase 2
0.6885	Remote Similarity	NPD8378	Approved
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD8296	Approved
0.6885	Remote Similarity	NPD8380	Approved
0.6885	Remote Similarity	NPD6015	Approved
0.6885	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8379	Approved
0.6885	Remote Similarity	NPD8335	Approved
0.688	Remote Similarity	NPD8293	Discontinued
0.6875	Remote Similarity	NPD5211	Phase 2
0.687	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6001	Approved
0.6847	Remote Similarity	NPD5286	Approved
0.6847	Remote Similarity	NPD4696	Approved
0.6847	Remote Similarity	NPD5285	Approved
0.6842	Remote Similarity	NPD4244	Approved
0.6842	Remote Similarity	NPD4245	Approved
0.6837	Remote Similarity	NPD6117	Approved
0.6829	Remote Similarity	NPD5988	Approved
0.6827	Remote Similarity	NPD3618	Phase 1
0.6827	Remote Similarity	NPD6098	Approved
0.6822	Remote Similarity	NPD6079	Approved
0.6818	Remote Similarity	NPD4755	Approved
0.6804	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6336	Discontinued
0.6792	Remote Similarity	NPD1695	Approved
0.6792	Remote Similarity	NPD5328	Approved
0.6792	Remote Similarity	NPD6051	Approved
0.6789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5223	Approved
0.6783	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6335	Approved
0.6765	Remote Similarity	NPD4223	Phase 3
0.6765	Remote Similarity	NPD4221	Approved
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4225	Approved
0.6754	Remote Similarity	NPD5141	Approved
0.6754	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6274	Approved
0.6748	Remote Similarity	NPD7503	Approved
0.6737	Remote Similarity	NPD3698	Phase 2
0.6735	Remote Similarity	NPD3702	Approved
0.6733	Remote Similarity	NPD6928	Phase 2
0.6731	Remote Similarity	NPD5329	Approved
0.6731	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5226	Approved
0.6726	Remote Similarity	NPD5225	Approved
0.6726	Remote Similarity	NPD5224	Approved
0.6726	Remote Similarity	NPD4633	Approved
0.6721	Remote Similarity	NPD7100	Approved
0.6721	Remote Similarity	NPD7101	Approved
0.6699	Remote Similarity	NPD5362	Discontinued
0.6698	Remote Similarity	NPD5208	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6694	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5174	Approved
0.664	Remote Similarity	NPD6067	Discontinued
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD6313	Approved
0.6635	Remote Similarity	NPD4197	Approved
0.661	Remote Similarity	NPD4634	Approved
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4251	Approved
0.6604	Remote Similarity	NPD4250	Approved
0.6598	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6081	Approved
0.6598	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5222	Approved
0.6577	Remote Similarity	NPD4697	Phase 3
0.6577	Remote Similarity	NPD5221	Approved
0.6574	Remote Similarity	NPD5692	Phase 3
0.6571	Remote Similarity	NPD5363	Approved
0.6571	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD6033	Approved
0.6525	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4754	Approved
0.6518	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD5694	Approved
0.6509	Remote Similarity	NPD4690	Approved
0.6509	Remote Similarity	NPD4688	Approved
0.6509	Remote Similarity	NPD4249	Approved
0.6509	Remote Similarity	NPD5690	Phase 2
0.6509	Remote Similarity	NPD5279	Phase 3
0.6509	Remote Similarity	NPD4689	Approved
0.6509	Remote Similarity	NPD5205	Approved
0.6509	Remote Similarity	NPD4138	Approved
0.6509	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4693	Phase 3

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