NPASS Compound

Structure

CID219353 OpenBabel06191716012D 28 30 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 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 0.8660 -1.5000 0.0000 C 0 0 0 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 -1.7321 1.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 -2.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 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 1.7321 1.0000 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 -0.0000 1.0000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 2.3660 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 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 23 2 0 0 0 0 11 21 1 0 0 0 0 11 28 1 0 0 0 0 13 24 2 0 0 0 0 13 28 1 0 0 0 0 14 12 1 6 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 1 0 0 0 17 22 1 1 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 26 2 0 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 21 1 1 0 0 0 20 22 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	405.594
LogP:	1.632
LogD:	0.987
LogS:	-2.263
# Rotatable Bonds:	5
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	5.104
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.928
MDCK Permeability:	2.6610505301505327e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.87
20% Bioavailability (F20%):	0.19
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797
Plasma Protein Binding (PPB):	57.21491622924805%
Volume Distribution (VD):	0.73
Pgp-substrate:	50.66464614868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.458
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	3.757
Half-life (T1/2):	0.726

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.355
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.341
Carcinogencity:	0.156
Eye Corrosion:	0.008
Eye Irritation:	0.016
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC219353

Natural Product ID:	NPC219353
*Common Name:**	Eriocasin D
IUPAC Name:	[(1R,4S,4aS,4bR,7R,8aR,10S,10aR)-4,10-dihydroxy-1,4a-dimethyl-9-oxo-7-(3-oxoprop-1-en-2-yl)-3,4,4b,5,6,7,8,8a,10,10a-decahydro-2H-phenanthren-1-yl]methyl acetate
Synonyms:	Eriocasin D
Standard InCHIKey:	HYXIZWTUHCHPMV-HQNQHPRXSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-12(10-23)14-5-6-16-15(9-14)18(26)19(27)20-21(3,11-28-13(2)24)8-7-17(25)22(16,20)4/h10,14-17,19-20,25,27H,1,5-9,11H2,2-4H3/t14-,15-,16-,17+,19-,20-,21+,22-/m1/s1
SMILES:	C=C(C=O)[C@@H]1CC[C@@H]2[C@@H](C1)C(=O)[C@H]([C@@H]1[C@@](C)(CC[C@@H]([C@@]21C)O)COC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641875
PubChem CID:	50901033
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[538251]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[538251]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	5700.0	nM	PMID[538251]

☑ 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 NPC219353 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	242
0.1-0.2	1746
0.2-0.3	5636
0.3-0.4	10414
0.4-0.5	10888
0.5-0.6	6574
0.6-0.7	4947
0.7-0.8	2090
0.8-0.85	118
0.85-0.9	37
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC293890
0.9556	High Similarity	NPC169751
0.9556	High Similarity	NPC272635
0.914	High Similarity	NPC29410
0.914	High Similarity	NPC200054
0.9032	High Similarity	NPC98639
0.8989	High Similarity	NPC34190
0.8947	High Similarity	NPC38296
0.8947	High Similarity	NPC162459
0.8947	High Similarity	NPC38471
0.8947	High Similarity	NPC98837
0.8947	High Similarity	NPC471038
0.8947	High Similarity	NPC28864
0.8947	High Similarity	NPC20479
0.8936	High Similarity	NPC329910
0.8913	High Similarity	NPC198054
0.8854	High Similarity	NPC293866
0.883	High Similarity	NPC470229
0.883	High Similarity	NPC470232
0.8812	High Similarity	NPC100908
0.8776	High Similarity	NPC95585
0.8776	High Similarity	NPC282233
0.8763	High Similarity	NPC252614
0.8763	High Similarity	NPC46848
0.875	High Similarity	NPC474793
0.875	High Similarity	NPC89099
0.8723	High Similarity	NPC470385
0.8723	High Similarity	NPC475118
0.8723	High Similarity	NPC47853
0.8723	High Similarity	NPC470386
0.87	High Similarity	NPC176949
0.87	High Similarity	NPC201908
0.8673	High Similarity	NPC275990
0.8646	High Similarity	NPC10864
0.8617	High Similarity	NPC294263
0.8586	High Similarity	NPC209298
0.8586	High Similarity	NPC96217
0.8586	High Similarity	NPC469985
0.8586	High Similarity	NPC87927
0.8586	High Similarity	NPC277074
0.8586	High Similarity	NPC122811
0.8571	High Similarity	NPC52899
0.8571	High Similarity	NPC148279
0.8571	High Similarity	NPC289148
0.8571	High Similarity	NPC163963
0.8571	High Similarity	NPC236585
0.8557	High Similarity	NPC26270
0.8542	High Similarity	NPC470387
0.8542	High Similarity	NPC165616
0.8511	High Similarity	NPC198242
0.8511	High Similarity	NPC211403
0.8511	High Similarity	NPC470230
0.85	High Similarity	NPC47281
0.85	High Similarity	NPC301787
0.8485	Intermediate Similarity	NPC88203
0.8485	Intermediate Similarity	NPC214946
0.8485	Intermediate Similarity	NPC148628
0.8485	Intermediate Similarity	NPC286519
0.8485	Intermediate Similarity	NPC304832
0.8485	Intermediate Similarity	NPC246736
0.8485	Intermediate Similarity	NPC76866
0.8469	Intermediate Similarity	NPC470388
0.8469	Intermediate Similarity	NPC287676
0.8431	Intermediate Similarity	NPC211224
0.8421	Intermediate Similarity	NPC199543
0.8416	Intermediate Similarity	NPC138908
0.8416	Intermediate Similarity	NPC222833
0.8416	Intermediate Similarity	NPC28791
0.8416	Intermediate Similarity	NPC50535
0.8416	Intermediate Similarity	NPC200957
0.84	Intermediate Similarity	NPC139347
0.8384	Intermediate Similarity	NPC253886
0.8384	Intermediate Similarity	NPC121218
0.8367	Intermediate Similarity	NPC476806
0.8367	Intermediate Similarity	NPC476807
0.8367	Intermediate Similarity	NPC16911
0.8367	Intermediate Similarity	NPC78427
0.8365	Intermediate Similarity	NPC470281
0.8351	Intermediate Similarity	NPC471039
0.8351	Intermediate Similarity	NPC256227
0.8333	Intermediate Similarity	NPC251824
0.8333	Intermediate Similarity	NPC86852
0.8333	Intermediate Similarity	NPC166993
0.8317	Intermediate Similarity	NPC29705
0.8317	Intermediate Similarity	NPC98603
0.8317	Intermediate Similarity	NPC310586
0.8316	Intermediate Similarity	NPC250753
0.83	Intermediate Similarity	NPC15396
0.83	Intermediate Similarity	NPC170615
0.8298	Intermediate Similarity	NPC471043
0.8283	Intermediate Similarity	NPC472972
0.8283	Intermediate Similarity	NPC267921
0.828	Intermediate Similarity	NPC153604
0.8252	Intermediate Similarity	NPC231278
0.8252	Intermediate Similarity	NPC112895
0.8252	Intermediate Similarity	NPC218123
0.8252	Intermediate Similarity	NPC273155
0.8252	Intermediate Similarity	NPC94529
0.8235	Intermediate Similarity	NPC265127
0.8229	Intermediate Similarity	NPC244356
0.8229	Intermediate Similarity	NPC224060
0.8218	Intermediate Similarity	NPC275583
0.8218	Intermediate Similarity	NPC216114
0.8182	Intermediate Similarity	NPC260149
0.8182	Intermediate Similarity	NPC58942
0.8182	Intermediate Similarity	NPC474724
0.8172	Intermediate Similarity	NPC471042
0.8163	Intermediate Similarity	NPC104568
0.8163	Intermediate Similarity	NPC13949
0.8163	Intermediate Similarity	NPC5532
0.8163	Intermediate Similarity	NPC61369
0.8163	Intermediate Similarity	NPC469545
0.8155	Intermediate Similarity	NPC144854
0.8155	Intermediate Similarity	NPC186054
0.8155	Intermediate Similarity	NPC3316
0.8144	Intermediate Similarity	NPC471040
0.8144	Intermediate Similarity	NPC469982
0.8137	Intermediate Similarity	NPC84928
0.8137	Intermediate Similarity	NPC96268
0.8125	Intermediate Similarity	NPC476934
0.8125	Intermediate Similarity	NPC99380
0.8119	Intermediate Similarity	NPC272472
0.81	Intermediate Similarity	NPC471041
0.81	Intermediate Similarity	NPC94906
0.8085	Intermediate Similarity	NPC259009
0.8081	Intermediate Similarity	NPC253586
0.8081	Intermediate Similarity	NPC96839
0.8077	Intermediate Similarity	NPC63841
0.8077	Intermediate Similarity	NPC277017
0.8077	Intermediate Similarity	NPC189075
0.8077	Intermediate Similarity	NPC154608
0.8077	Intermediate Similarity	NPC275539
0.8077	Intermediate Similarity	NPC192813
0.8077	Intermediate Similarity	NPC293850
0.8061	Intermediate Similarity	NPC210214
0.8061	Intermediate Similarity	NPC473240
0.8061	Intermediate Similarity	NPC259042
0.8061	Intermediate Similarity	NPC274417
0.8061	Intermediate Similarity	NPC474727
0.8061	Intermediate Similarity	NPC157686
0.8061	Intermediate Similarity	NPC139570
0.8058	Intermediate Similarity	NPC37600
0.8058	Intermediate Similarity	NPC295366
0.8058	Intermediate Similarity	NPC278628
0.8058	Intermediate Similarity	NPC231530
0.8043	Intermediate Similarity	NPC471037
0.8041	Intermediate Similarity	NPC477435
0.8041	Intermediate Similarity	NPC477436
0.8041	Intermediate Similarity	NPC147272
0.8039	Intermediate Similarity	NPC95899
0.8039	Intermediate Similarity	NPC478057
0.8039	Intermediate Similarity	NPC159442
0.8039	Intermediate Similarity	NPC225238
0.8037	Intermediate Similarity	NPC202889
0.8021	Intermediate Similarity	NPC80401
0.8021	Intermediate Similarity	NPC328141
0.802	Intermediate Similarity	NPC471790
0.802	Intermediate Similarity	NPC295276
0.802	Intermediate Similarity	NPC71706
0.802	Intermediate Similarity	NPC471412
0.802	Intermediate Similarity	NPC14634
0.802	Intermediate Similarity	NPC75941
0.8019	Intermediate Similarity	NPC329953
0.8	Intermediate Similarity	NPC109059
0.8	Intermediate Similarity	NPC27814
0.8	Intermediate Similarity	NPC471966
0.8	Intermediate Similarity	NPC472028
0.8	Intermediate Similarity	NPC17183
0.8	Intermediate Similarity	NPC3032
0.8	Intermediate Similarity	NPC473319
0.8	Intermediate Similarity	NPC288
0.8	Intermediate Similarity	NPC131104
0.8	Intermediate Similarity	NPC475876
0.8	Intermediate Similarity	NPC236459
0.8	Intermediate Similarity	NPC477653
0.7981	Intermediate Similarity	NPC110496
0.7981	Intermediate Similarity	NPC88833
0.7981	Intermediate Similarity	NPC78966
0.7981	Intermediate Similarity	NPC471474
0.7981	Intermediate Similarity	NPC61071
0.7981	Intermediate Similarity	NPC284732
0.7981	Intermediate Similarity	NPC96333
0.798	Intermediate Similarity	NPC135548
0.798	Intermediate Similarity	NPC476318
0.798	Intermediate Similarity	NPC264979
0.798	Intermediate Similarity	NPC476327
0.798	Intermediate Similarity	NPC317573
0.798	Intermediate Similarity	NPC223169
0.7979	Intermediate Similarity	NPC185638
0.7979	Intermediate Similarity	NPC248216
0.7961	Intermediate Similarity	NPC474558
0.7961	Intermediate Similarity	NPC101842
0.7961	Intermediate Similarity	NPC202793
0.7961	Intermediate Similarity	NPC13149
0.7959	Intermediate Similarity	NPC469596
0.7959	Intermediate Similarity	NPC191094
0.7959	Intermediate Similarity	NPC302008
0.7959	Intermediate Similarity	NPC225474
0.7959	Intermediate Similarity	NPC303863
0.7959	Intermediate Similarity	NPC148000

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 NPC219353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	2235
0.2-0.3	3814
0.3-0.4	1811
0.4-0.5	598
0.5-0.6	232
0.6-0.7	130
0.7-0.8	85
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
0.7905	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD6899	Approved
0.7885	Intermediate Similarity	NPD7128	Approved
0.7885	Intermediate Similarity	NPD6402	Approved
0.7885	Intermediate Similarity	NPD6675	Approved
0.7885	Intermediate Similarity	NPD5739	Approved
0.781	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD7748	Approved
0.7757	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7102	Approved
0.7755	Intermediate Similarity	NPD8035	Phase 2
0.7755	Intermediate Similarity	NPD8034	Phase 2
0.7755	Intermediate Similarity	NPD7515	Phase 2
0.7736	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6011	Approved
0.7736	Intermediate Similarity	NPD7320	Approved
0.7723	Intermediate Similarity	NPD7902	Approved
0.7706	Intermediate Similarity	NPD4632	Approved
0.7685	Intermediate Similarity	NPD6649	Approved
0.7685	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD8130	Phase 1
0.7685	Intermediate Similarity	NPD6650	Approved
0.7685	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6617	Approved
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6373	Approved
0.7664	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7642	Intermediate Similarity	NPD5701	Approved
0.7624	Intermediate Similarity	NPD4697	Phase 3
0.7615	Intermediate Similarity	NPD8297	Approved
0.7615	Intermediate Similarity	NPD6882	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6009	Approved
0.7456	Intermediate Similarity	NPD6319	Approved
0.7451	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5222	Approved
0.7451	Intermediate Similarity	NPD5221	Approved
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7604	Phase 2
0.7414	Intermediate Similarity	NPD8328	Phase 3
0.7404	Intermediate Similarity	NPD5285	Approved
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.74	Intermediate Similarity	NPD6079	Approved
0.7391	Intermediate Similarity	NPD5983	Phase 2
0.7379	Intermediate Similarity	NPD4755	Approved
0.7379	Intermediate Similarity	NPD5173	Approved
0.7374	Intermediate Similarity	NPD5328	Approved
0.735	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD5223	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7311	Intermediate Similarity	NPD7736	Approved
0.7304	Intermediate Similarity	NPD6054	Approved
0.7288	Intermediate Similarity	NPD6336	Discontinued
0.7288	Intermediate Similarity	NPD6616	Approved
0.7281	Intermediate Similarity	NPD6335	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7257	Intermediate Similarity	NPD6868	Approved
0.7257	Intermediate Similarity	NPD6274	Approved
0.7238	Intermediate Similarity	NPD4700	Approved
0.7227	Intermediate Similarity	NPD7078	Approved
0.7222	Intermediate Similarity	NPD6008	Approved
0.7217	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD7101	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7193	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6317	Approved
0.7179	Intermediate Similarity	NPD6370	Approved
0.7174	Intermediate Similarity	NPD3703	Phase 2
0.7172	Intermediate Similarity	NPD3573	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD5141	Approved
0.713	Intermediate Similarity	NPD6314	Approved
0.713	Intermediate Similarity	NPD6313	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7113	Intermediate Similarity	NPD4788	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.71	Intermediate Similarity	NPD5737	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7094	Intermediate Similarity	NPD6015	Approved
0.7094	Intermediate Similarity	NPD6016	Approved
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.7071	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD4754	Approved
0.7034	Intermediate Similarity	NPD5988	Approved
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7319	Approved
0.6949	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6909	Approved
0.6949	Remote Similarity	NPD6908	Approved
0.6949	Remote Similarity	NPD6921	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6937	Remote Similarity	NPD6686	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8133	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.69	Remote Similarity	NPD7146	Approved
0.69	Remote Similarity	NPD6409	Approved
0.69	Remote Similarity	NPD7334	Approved
0.69	Remote Similarity	NPD7521	Approved
0.69	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD6684	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4786	Approved
0.6863	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5695	Phase 3
0.6847	Remote Similarity	NPD6412	Phase 2
0.6837	Remote Similarity	NPD3667	Approved
0.6827	Remote Similarity	NPD4202	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5169	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5250	Approved
0.6814	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4695	Discontinued
0.6786	Remote Similarity	NPD5168	Approved
0.6765	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD5216	Approved
0.6754	Remote Similarity	NPD5217	Approved
0.6754	Remote Similarity	NPD5215	Approved
0.6754	Remote Similarity	NPD5127	Approved
0.6748	Remote Similarity	NPD6033	Approved
0.67	Remote Similarity	NPD3666	Approved
0.67	Remote Similarity	NPD3133	Approved
0.67	Remote Similarity	NPD3665	Phase 1
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD4753	Phase 2
0.6699	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7115	Discovery
0.6581	Remote Similarity	NPD5167	Approved
0.6569	Remote Similarity	NPD6098	Approved
0.6569	Remote Similarity	NPD5279	Phase 3
0.6559	Remote Similarity	NPD4789	Approved
0.6542	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4629	Approved
0.6542	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD6333	Approved
0.6538	Remote Similarity	NPD6334	Approved
0.6531	Remote Similarity	NPD7645	Phase 2
0.6514	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5777	Approved
0.6481	Remote Similarity	NPD7614	Phase 1
0.6471	Remote Similarity	NPD5329	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6423	Remote Similarity	NPD6067	Discontinued
0.6415	Remote Similarity	NPD5693	Phase 1
0.6415	Remote Similarity	NPD6050	Approved
0.641	Remote Similarity	NPD6053	Discontinued
0.6408	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4245	Approved
0.6383	Remote Similarity	NPD4244	Approved
0.6373	Remote Similarity	NPD3668	Phase 3
0.6373	Remote Similarity	NPD4197	Approved
0.6372	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6435	Approved
0.633	Remote Similarity	NPD7732	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