NPASS Compound

Structure

CID198054 OpenBabel06191715582D 27 29 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 13 24 2 0 0 0 0 13 27 1 0 0 0 0 14 12 1 6 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 1 0 0 0 17 22 1 1 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 1 0 0 0 22 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	2.767
LogD:	2.617
LogS:	-2.768
# Rotatable Bonds:	4
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	4.946
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.714
MDCK Permeability:	6.790541374357417e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.495
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	55.18349838256836%
Volume Distribution (VD):	0.808
Pgp-substrate:	56.48351287841797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.601
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.153
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	6.36
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.453
Maximum Recommended Daily Dose:	0.627
Skin Sensitization:	0.305
Carcinogencity:	0.395
Eye Corrosion:	0.187
Eye Irritation:	0.054
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC198054

Natural Product ID:	NPC198054
*Common Name:**	Eriocasin E
IUPAC Name:	[(2S,4R,4aR,4bS,8aR,9S,10aR)-9-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-4b,8,8-trimethyl-10-oxo-2,3,4,4a,5,6,7,8a,9,10a-decahydro-1H-phenanthren-4-yl] acetate
Synonyms:	Eriocasin E
Standard InCHIKey:	LSHXXXQWPVHVRD-XONTYPPSSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-12(11-23)14-9-15-17(16(10-14)27-13(2)24)22(5)8-6-7-21(3,4)20(22)19(26)18(15)25/h14-17,19-20,23,26H,1,6-11H2,2-5H3/t14-,15+,16+,17-,19+,20+,22-/m0/s1
SMILES:	C=C(CO)[C@H]1C[C@@H]2[C@@H]([C@@H](C1)OC(=O)C)[C@]1(C)CCCC(C)(C)[C@H]1[C@@H](C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641890
PubChem CID:	50901036
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[489588]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[489588]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[489588]

☑ 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 NPC198054 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	227
0.1-0.2	1595
0.2-0.3	5057
0.3-0.4	11105
0.4-0.5	10865
0.5-0.6	6185
0.6-0.7	5058
0.7-0.8	2426
0.8-0.85	161
0.85-0.9	16
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC199543
0.8913	High Similarity	NPC219353
0.8854	High Similarity	NPC47281
0.8778	High Similarity	NPC232202
0.8763	High Similarity	NPC50535
0.875	High Similarity	NPC469985
0.8737	High Similarity	NPC253886
0.8737	High Similarity	NPC121218
0.871	High Similarity	NPC200054
0.871	High Similarity	NPC29410
0.8696	High Similarity	NPC47853
0.8696	High Similarity	NPC469982
0.8632	High Similarity	NPC293890
0.8602	High Similarity	NPC98639
0.8571	High Similarity	NPC28791
0.8557	High Similarity	NPC478057
0.8542	High Similarity	NPC295276
0.8539	High Similarity	NPC187545
0.8526	High Similarity	NPC78427
0.8526	High Similarity	NPC20479
0.8526	High Similarity	NPC162459
0.8526	High Similarity	NPC477653
0.8526	High Similarity	NPC38296
0.8526	High Similarity	NPC38471
0.8526	High Similarity	NPC471038
0.8526	High Similarity	NPC28864
0.8526	High Similarity	NPC98837
0.8526	High Similarity	NPC16911
0.8523	High Similarity	NPC97505
0.8511	High Similarity	NPC329910
0.8495	Intermediate Similarity	NPC272635
0.8495	Intermediate Similarity	NPC169751
0.8485	Intermediate Similarity	NPC86852
0.8485	Intermediate Similarity	NPC251824
0.8462	Intermediate Similarity	NPC194642
0.8454	Intermediate Similarity	NPC170615
0.8438	Intermediate Similarity	NPC293866
0.8438	Intermediate Similarity	NPC287676
0.8427	Intermediate Similarity	NPC164424
0.8409	Intermediate Similarity	NPC471037
0.8404	Intermediate Similarity	NPC470232
0.8404	Intermediate Similarity	NPC474727
0.8404	Intermediate Similarity	NPC470229
0.8387	Intermediate Similarity	NPC147272
0.8387	Intermediate Similarity	NPC294263
0.8387	Intermediate Similarity	NPC224060
0.8387	Intermediate Similarity	NPC244356
0.8384	Intermediate Similarity	NPC37600
0.837	Intermediate Similarity	NPC46758
0.8367	Intermediate Similarity	NPC95899
0.8352	Intermediate Similarity	NPC16377
0.8352	Intermediate Similarity	NPC474719
0.8351	Intermediate Similarity	NPC46848
0.8351	Intermediate Similarity	NPC75941
0.8351	Intermediate Similarity	NPC289148
0.8351	Intermediate Similarity	NPC477053
0.8351	Intermediate Similarity	NPC163963
0.8351	Intermediate Similarity	NPC52899
0.8351	Intermediate Similarity	NPC477051
0.8351	Intermediate Similarity	NPC477052
0.8351	Intermediate Similarity	NPC252614
0.8333	Intermediate Similarity	NPC89099
0.8333	Intermediate Similarity	NPC322159
0.8333	Intermediate Similarity	NPC474724
0.8316	Intermediate Similarity	NPC256227
0.8315	Intermediate Similarity	NPC299963
0.83	Intermediate Similarity	NPC176949
0.83	Intermediate Similarity	NPC201908
0.8298	Intermediate Similarity	NPC470385
0.8298	Intermediate Similarity	NPC475118
0.8298	Intermediate Similarity	NPC470386
0.8295	Intermediate Similarity	NPC472504
0.8283	Intermediate Similarity	NPC29705
0.828	Intermediate Similarity	NPC474525
0.8265	Intermediate Similarity	NPC246736
0.8265	Intermediate Similarity	NPC286519
0.8265	Intermediate Similarity	NPC477054
0.8265	Intermediate Similarity	NPC88203
0.8265	Intermediate Similarity	NPC304832
0.8265	Intermediate Similarity	NPC214946
0.8265	Intermediate Similarity	NPC275990
0.8265	Intermediate Similarity	NPC76866
0.8265	Intermediate Similarity	NPC148628
0.8261	Intermediate Similarity	NPC116620
0.8261	Intermediate Similarity	NPC471043
0.8247	Intermediate Similarity	NPC41971
0.8247	Intermediate Similarity	NPC37047
0.8247	Intermediate Similarity	NPC180733
0.8242	Intermediate Similarity	NPC33768
0.8229	Intermediate Similarity	NPC476879
0.8229	Intermediate Similarity	NPC10864
0.8229	Intermediate Similarity	NPC476878
0.8229	Intermediate Similarity	NPC253586
0.8211	Intermediate Similarity	NPC210214
0.8211	Intermediate Similarity	NPC157686
0.8211	Intermediate Similarity	NPC259042
0.8211	Intermediate Similarity	NPC279974
0.82	Intermediate Similarity	NPC295366
0.8182	Intermediate Similarity	NPC122811
0.8182	Intermediate Similarity	NPC275583
0.8182	Intermediate Similarity	NPC282233
0.8182	Intermediate Similarity	NPC87927
0.8182	Intermediate Similarity	NPC95585
0.8182	Intermediate Similarity	NPC209298
0.8182	Intermediate Similarity	NPC277074
0.8182	Intermediate Similarity	NPC328264
0.8182	Intermediate Similarity	NPC266
0.8172	Intermediate Similarity	NPC123252
0.8172	Intermediate Similarity	NPC153853
0.8172	Intermediate Similarity	NPC219937
0.8172	Intermediate Similarity	NPC291028
0.8172	Intermediate Similarity	NPC194485
0.8172	Intermediate Similarity	NPC100313
0.8172	Intermediate Similarity	NPC53890
0.8172	Intermediate Similarity	NPC46441
0.8163	Intermediate Similarity	NPC118964
0.8152	Intermediate Similarity	NPC160304
0.8152	Intermediate Similarity	NPC4309
0.8144	Intermediate Similarity	NPC474793
0.8144	Intermediate Similarity	NPC478056
0.8144	Intermediate Similarity	NPC119036
0.814	Intermediate Similarity	NPC474433
0.8137	Intermediate Similarity	NPC141350
0.8132	Intermediate Similarity	NPC325594
0.8132	Intermediate Similarity	NPC472738
0.8132	Intermediate Similarity	NPC73038
0.8132	Intermediate Similarity	NPC12774
0.8132	Intermediate Similarity	NPC2783
0.8132	Intermediate Similarity	NPC70661
0.8132	Intermediate Similarity	NPC185638
0.8125	Intermediate Similarity	NPC157113
0.8125	Intermediate Similarity	NPC62516
0.8125	Intermediate Similarity	NPC470387
0.8125	Intermediate Similarity	NPC223169
0.8125	Intermediate Similarity	NPC317573
0.8111	Intermediate Similarity	NPC263974
0.8105	Intermediate Similarity	NPC148000
0.8105	Intermediate Similarity	NPC225474
0.8105	Intermediate Similarity	NPC469596
0.8105	Intermediate Similarity	NPC24861
0.81	Intermediate Similarity	NPC98603
0.81	Intermediate Similarity	NPC301787
0.8085	Intermediate Similarity	NPC211403
0.8085	Intermediate Similarity	NPC250753
0.8085	Intermediate Similarity	NPC160506
0.8085	Intermediate Similarity	NPC198242
0.8085	Intermediate Similarity	NPC105189
0.8085	Intermediate Similarity	NPC470230
0.8077	Intermediate Similarity	NPC40608
0.8061	Intermediate Similarity	NPC251680
0.8061	Intermediate Similarity	NPC108371
0.8061	Intermediate Similarity	NPC470388
0.8061	Intermediate Similarity	NPC471041
0.8061	Intermediate Similarity	NPC327431
0.8061	Intermediate Similarity	NPC94906
0.8061	Intermediate Similarity	NPC472972
0.8058	Intermediate Similarity	NPC100908
0.8043	Intermediate Similarity	NPC181103
0.8043	Intermediate Similarity	NPC175293
0.8043	Intermediate Similarity	NPC269360
0.8043	Intermediate Similarity	NPC153604
0.8043	Intermediate Similarity	NPC470920
0.8043	Intermediate Similarity	NPC264005
0.8041	Intermediate Similarity	NPC470425
0.8041	Intermediate Similarity	NPC189880
0.8041	Intermediate Similarity	NPC473963
0.8041	Intermediate Similarity	NPC272451
0.8039	Intermediate Similarity	NPC94529
0.8039	Intermediate Similarity	NPC211224
0.8022	Intermediate Similarity	NPC477445
0.8022	Intermediate Similarity	NPC292553
0.8022	Intermediate Similarity	NPC294438
0.8022	Intermediate Similarity	NPC264317
0.8021	Intermediate Similarity	NPC197158
0.8021	Intermediate Similarity	NPC471624
0.802	Intermediate Similarity	NPC200957
0.802	Intermediate Similarity	NPC222833
0.802	Intermediate Similarity	NPC138908
0.8	Intermediate Similarity	NPC107674
0.8	Intermediate Similarity	NPC49776
0.8	Intermediate Similarity	NPC473690
0.8	Intermediate Similarity	NPC141497
0.8	Intermediate Similarity	NPC170220
0.8	Intermediate Similarity	NPC216114
0.8	Intermediate Similarity	NPC475061
0.8	Intermediate Similarity	NPC474436
0.8	Intermediate Similarity	NPC295643
0.8	Intermediate Similarity	NPC214756
0.8	Intermediate Similarity	NPC471902
0.8	Intermediate Similarity	NPC139347
0.8	Intermediate Similarity	NPC243347
0.8	Intermediate Similarity	NPC26046
0.8	Intermediate Similarity	NPC63118
0.8	Intermediate Similarity	NPC225238
0.8	Intermediate Similarity	NPC272075
0.8	Intermediate Similarity	NPC86368
0.8	Intermediate Similarity	NPC291373
0.8	Intermediate Similarity	NPC287118
0.7981	Intermediate Similarity	NPC470281
0.7981	Intermediate Similarity	NPC157476

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 NPC198054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	2036
0.2-0.3	3751
0.3-0.4	2024
0.4-0.5	651
0.5-0.6	231
0.6-0.7	193
0.7-0.8	44
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
0.8085	Intermediate Similarity	NPD8035	Phase 2
0.8085	Intermediate Similarity	NPD8034	Phase 2
0.8061	Intermediate Similarity	NPD7640	Approved
0.8061	Intermediate Similarity	NPD7639	Approved
0.8022	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7638	Approved
0.7917	Intermediate Similarity	NPD7748	Approved
0.7895	Intermediate Similarity	NPD7515	Phase 2
0.7864	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7902	Approved
0.764	Intermediate Similarity	NPD6118	Approved
0.764	Intermediate Similarity	NPD6114	Approved
0.764	Intermediate Similarity	NPD6115	Approved
0.764	Intermediate Similarity	NPD6697	Approved
0.7629	Intermediate Similarity	NPD6399	Phase 3
0.7551	Intermediate Similarity	NPD7900	Approved
0.7551	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7632	Discontinued
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7453	Intermediate Similarity	NPD6373	Approved
0.7453	Intermediate Similarity	NPD6372	Approved
0.7416	Intermediate Similarity	NPD6117	Approved
0.7368	Intermediate Similarity	NPD3618	Phase 1
0.7358	Intermediate Similarity	NPD7320	Approved
0.7358	Intermediate Similarity	NPD6899	Approved
0.7358	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6116	Phase 1
0.7327	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD6083	Phase 2
0.7315	Intermediate Similarity	NPD6650	Approved
0.7315	Intermediate Similarity	NPD6649	Approved
0.729	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5701	Approved
0.7264	Intermediate Similarity	NPD5697	Approved
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7222	Intermediate Similarity	NPD6883	Approved
0.7222	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD7290	Approved
0.7217	Intermediate Similarity	NPD8328	Phase 3
0.7216	Intermediate Similarity	NPD6672	Approved
0.7216	Intermediate Similarity	NPD5737	Approved
0.7196	Intermediate Similarity	NPD6011	Approved
0.7191	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4632	Approved
0.7182	Intermediate Similarity	NPD8133	Approved
0.7158	Intermediate Similarity	NPD4786	Approved
0.7156	Intermediate Similarity	NPD8130	Phase 1
0.7156	Intermediate Similarity	NPD6617	Approved
0.7156	Intermediate Similarity	NPD6869	Approved
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5328	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.7128	Intermediate Similarity	NPD3667	Approved
0.7111	Intermediate Similarity	NPD3703	Phase 2
0.7091	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD8297	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD5222	Approved
0.7053	Intermediate Similarity	NPD4788	Approved
0.7048	Intermediate Similarity	NPD5211	Phase 2
0.7043	Intermediate Similarity	NPD6921	Approved
0.7041	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7521	Approved
0.701	Intermediate Similarity	NPD7146	Approved
0.701	Intermediate Similarity	NPD7334	Approved
0.701	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD6684	Approved
0.701	Intermediate Similarity	NPD6409	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD6079	Approved
0.6991	Remote Similarity	NPD7115	Discovery
0.6991	Remote Similarity	NPD6009	Approved
0.699	Remote Similarity	NPD5173	Approved
0.699	Remote Similarity	NPD4755	Approved
0.6972	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5695	Phase 3
0.6957	Remote Similarity	NPD6319	Approved
0.6932	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD4225	Approved
0.6916	Remote Similarity	NPD5141	Approved
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6868	Approved
0.6897	Remote Similarity	NPD5983	Phase 2
0.6881	Remote Similarity	NPD6686	Approved
0.6869	Remote Similarity	NPD6903	Approved
0.6864	Remote Similarity	NPD7492	Approved
0.6857	Remote Similarity	NPD5285	Approved
0.6857	Remote Similarity	NPD5286	Approved
0.6857	Remote Similarity	NPD4700	Approved
0.6857	Remote Similarity	NPD4696	Approved
0.6854	Remote Similarity	NPD4789	Approved
0.6837	Remote Similarity	NPD6098	Approved
0.6833	Remote Similarity	NPD7736	Approved
0.6832	Remote Similarity	NPD6411	Approved
0.681	Remote Similarity	NPD6054	Approved
0.681	Remote Similarity	NPD6059	Approved
0.6809	Remote Similarity	NPD7645	Phase 2
0.6807	Remote Similarity	NPD6616	Approved
0.6807	Remote Similarity	NPD6336	Discontinued
0.6804	Remote Similarity	NPD3666	Approved
0.6804	Remote Similarity	NPD3665	Phase 1
0.6804	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD4753	Phase 2
0.68	Remote Similarity	NPD6904	Approved
0.6796	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5223	Approved
0.6789	Remote Similarity	NPD6412	Phase 2
0.6783	Remote Similarity	NPD6335	Approved
0.6778	Remote Similarity	NPD5777	Approved
0.6768	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD4202	Approved
0.6754	Remote Similarity	NPD6274	Approved
0.675	Remote Similarity	NPD7078	Approved
0.675	Remote Similarity	NPD8293	Discontinued
0.6737	Remote Similarity	NPD4695	Discontinued
0.6737	Remote Similarity	NPD7525	Registered
0.6729	Remote Similarity	NPD5226	Approved
0.6729	Remote Similarity	NPD5225	Approved
0.6729	Remote Similarity	NPD4633	Approved
0.6729	Remote Similarity	NPD5224	Approved
0.6724	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7101	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6695	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6314	Approved
0.6638	Remote Similarity	NPD6313	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4629	Approved
0.6635	Remote Similarity	NPD5210	Approved
0.6634	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6101	Approved
0.6633	Remote Similarity	NPD3668	Phase 3
0.661	Remote Similarity	NPD6015	Approved
0.661	Remote Similarity	NPD6016	Approved
0.661	Remote Similarity	NPD6909	Approved
0.661	Remote Similarity	NPD6908	Approved
0.661	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4634	Approved
0.6598	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6081	Approved
0.6591	Remote Similarity	NPD4224	Phase 2
0.6566	Remote Similarity	NPD1694	Approved
0.6566	Remote Similarity	NPD5329	Approved
0.6556	Remote Similarity	NPD3698	Phase 2
0.6555	Remote Similarity	NPD5988	Approved
0.6545	Remote Similarity	NPD4767	Approved
0.6545	Remote Similarity	NPD4768	Approved
0.6526	Remote Similarity	NPD3617	Approved
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6050	Approved
0.6504	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4197	Approved
0.6444	Remote Similarity	NPD5360	Phase 3
0.6444	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5168	Approved
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6429	Remote Similarity	NPD5128	Approved
0.6423	Remote Similarity	NPD6033	Approved
0.6408	Remote Similarity	NPD5692	Phase 3
0.6383	Remote Similarity	NPD3702	Approved
0.6381	Remote Similarity	NPD5282	Discontinued
0.6381	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD6067	Discontinued
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6354	Remote Similarity	NPD3671	Phase 1
0.6346	Remote Similarity	NPD5281	Approved
0.6346	Remote Similarity	NPD5694	Approved
0.6346	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD4519	Discontinued

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