NPASS Compound

Structure

CID272635 OpenBabel06191716082D 31 33 0 0 1 0 0 0 0 0999 V2000 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 0.0000 -2.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 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 2 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 -2.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 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 0.8660 -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 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 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 3.4641 0.0000 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 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 25 2 0 0 0 0 12 24 1 0 0 0 0 12 30 1 0 0 0 0 14 26 2 0 0 0 0 14 30 1 0 0 0 0 15 27 2 0 0 0 0 15 31 1 0 0 0 0 16 13 1 6 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 1 0 0 0 19 24 1 6 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 28 2 0 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 23 4 1 1 0 0 0 24 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	446.34
LogP:	2.167
LogD:	1.129
LogS:	-2.612
# Rotatable Bonds:	7
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	4.934
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.86
MDCK Permeability:	7.522931991843507e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.887
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.595

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.554
Plasma Protein Binding (PPB):	61.06064987182617%
Volume Distribution (VD):	1.006
Pgp-substrate:	45.59678649902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.297
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.428
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	3.097
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.297
Drug-inuced Liver Injury (DILI):	0.55
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.821
Skin Sensitization:	0.435
Carcinogencity:	0.179
Eye Corrosion:	0.045
Eye Irritation:	0.038
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC272635

Natural Product ID:	NPC272635
*Common Name:**	6Beta,19-Diacetoxy-6Beta-Hydroxy-7,16-Dioxo-Ent-Abieta-15(17)-Ene
IUPAC Name:	[(1R,2S,4aS,4bR,7R,8aR,10S,10aS)-2-acetyloxy-10-hydroxy-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:	3-acetyleriocasin C
Standard InCHIKey:	LKBMNVLYWWORRA-QLKQUVKYSA-N
Standard InCHI:	InChI=1S/C24H34O7/c1-13(11-25)16-6-7-18-17(10-16)20(28)21(29)22-23(18,4)9-8-19(31-15(3)27)24(22,5)12-30-14(2)26/h11,16-19,21-22,29H,1,6-10,12H2,2-5H3/t16-,17-,18-,19+,21-,22+,23+,24-/m1/s1
SMILES:	O=CC(=C)[C@@H]1CC[C@@H]2[C@@H](C1)C(=O)[C@H]([C@H]1[C@@]2(C)CC[C@@H]([C@@]1(C)COC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641889
PubChem CID:	50901034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003238] 7-hydroxysteroids [CHEMONTID:0003239] 7-alpha-hydroxysteroids

*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[558466]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[558466]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[558466]

☑ 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 NPC272635 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	231
0.1-0.2	1710
0.2-0.3	5776
0.3-0.4	11603
0.4-0.5	9976
0.5-0.6	6513
0.6-0.7	4875
0.7-0.8	1869
0.8-0.85	115
0.85-0.9	24
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169751
0.9556	High Similarity	NPC219353
0.9457	High Similarity	NPC293890
0.9195	High Similarity	NPC34190
0.9011	High Similarity	NPC294263
0.8817	High Similarity	NPC98639
0.8737	High Similarity	NPC38296
0.8737	High Similarity	NPC162459
0.8737	High Similarity	NPC38471
0.8737	High Similarity	NPC20479
0.8737	High Similarity	NPC98837
0.8737	High Similarity	NPC28864
0.8723	High Similarity	NPC200054
0.8723	High Similarity	NPC165616
0.8723	High Similarity	NPC29410
0.8646	High Similarity	NPC293866
0.8632	High Similarity	NPC10864
0.8614	High Similarity	NPC100908
0.8586	High Similarity	NPC265127
0.8557	High Similarity	NPC148279
0.8557	High Similarity	NPC46848
0.8542	High Similarity	NPC89099
0.8542	High Similarity	NPC474793
0.8542	High Similarity	NPC471038
0.8526	High Similarity	NPC13949
0.8526	High Similarity	NPC329910
0.8526	High Similarity	NPC471039
0.85	High Similarity	NPC176949
0.85	High Similarity	NPC201908
0.8495	Intermediate Similarity	NPC250753
0.8495	Intermediate Similarity	NPC198054
0.8469	Intermediate Similarity	NPC275990
0.8421	Intermediate Similarity	NPC470229
0.8421	Intermediate Similarity	NPC210214
0.8421	Intermediate Similarity	NPC470232
0.8404	Intermediate Similarity	NPC477436
0.8404	Intermediate Similarity	NPC477435
0.8384	Intermediate Similarity	NPC95585
0.8384	Intermediate Similarity	NPC282233
0.8384	Intermediate Similarity	NPC96217
0.8384	Intermediate Similarity	NPC87927
0.8367	Intermediate Similarity	NPC163963
0.8367	Intermediate Similarity	NPC52899
0.8367	Intermediate Similarity	NPC252614
0.8367	Intermediate Similarity	NPC289148
0.8367	Intermediate Similarity	NPC236585
0.8352	Intermediate Similarity	NPC471042
0.8351	Intermediate Similarity	NPC26270
0.8333	Intermediate Similarity	NPC104568
0.8316	Intermediate Similarity	NPC475118
0.8316	Intermediate Similarity	NPC471040
0.8316	Intermediate Similarity	NPC470386
0.8316	Intermediate Similarity	NPC47853
0.8316	Intermediate Similarity	NPC470385
0.83	Intermediate Similarity	NPC47281
0.83	Intermediate Similarity	NPC301787
0.8298	Intermediate Similarity	NPC211403
0.8298	Intermediate Similarity	NPC198242
0.8298	Intermediate Similarity	NPC99380
0.8283	Intermediate Similarity	NPC76866
0.8283	Intermediate Similarity	NPC286519
0.8283	Intermediate Similarity	NPC88203
0.8283	Intermediate Similarity	NPC246736
0.8283	Intermediate Similarity	NPC304832
0.8283	Intermediate Similarity	NPC214946
0.8283	Intermediate Similarity	NPC148628
0.8265	Intermediate Similarity	NPC287676
0.8261	Intermediate Similarity	NPC174619
0.8235	Intermediate Similarity	NPC211224
0.8229	Intermediate Similarity	NPC274417
0.8229	Intermediate Similarity	NPC477438
0.8229	Intermediate Similarity	NPC29112
0.8229	Intermediate Similarity	NPC477437
0.8229	Intermediate Similarity	NPC142352
0.8229	Intermediate Similarity	NPC139570
0.8222	Intermediate Similarity	NPC471037
0.8218	Intermediate Similarity	NPC200957
0.8218	Intermediate Similarity	NPC222833
0.8218	Intermediate Similarity	NPC138908
0.8218	Intermediate Similarity	NPC28791
0.8218	Intermediate Similarity	NPC50535
0.8211	Intermediate Similarity	NPC59350
0.82	Intermediate Similarity	NPC139347
0.82	Intermediate Similarity	NPC470310
0.82	Intermediate Similarity	NPC469985
0.82	Intermediate Similarity	NPC277074
0.82	Intermediate Similarity	NPC209298
0.82	Intermediate Similarity	NPC122811
0.8191	Intermediate Similarity	NPC328141
0.8182	Intermediate Similarity	NPC60947
0.8182	Intermediate Similarity	NPC121218
0.8182	Intermediate Similarity	NPC253886
0.8163	Intermediate Similarity	NPC109059
0.8163	Intermediate Similarity	NPC288
0.8163	Intermediate Similarity	NPC476806
0.8163	Intermediate Similarity	NPC476807
0.8163	Intermediate Similarity	NPC16911
0.8163	Intermediate Similarity	NPC471966
0.8163	Intermediate Similarity	NPC78427
0.8161	Intermediate Similarity	NPC474433
0.8152	Intermediate Similarity	NPC185638
0.8144	Intermediate Similarity	NPC470387
0.8144	Intermediate Similarity	NPC223169
0.8137	Intermediate Similarity	NPC44063
0.8137	Intermediate Similarity	NPC86852
0.8137	Intermediate Similarity	NPC166993
0.8137	Intermediate Similarity	NPC251824
0.8132	Intermediate Similarity	NPC146683
0.8125	Intermediate Similarity	NPC303863
0.8125	Intermediate Similarity	NPC293086
0.8125	Intermediate Similarity	NPC269729
0.8125	Intermediate Similarity	NPC477439
0.8125	Intermediate Similarity	NPC469982
0.8119	Intermediate Similarity	NPC98603
0.8105	Intermediate Similarity	NPC474525
0.8105	Intermediate Similarity	NPC470230
0.81	Intermediate Similarity	NPC15396
0.81	Intermediate Similarity	NPC170615
0.81	Intermediate Similarity	NPC136289
0.8081	Intermediate Similarity	NPC475202
0.8081	Intermediate Similarity	NPC470388
0.8081	Intermediate Similarity	NPC475385
0.8081	Intermediate Similarity	NPC475392
0.8068	Intermediate Similarity	NPC476810
0.8065	Intermediate Similarity	NPC476932
0.8065	Intermediate Similarity	NPC33768
0.8065	Intermediate Similarity	NPC153604
0.8065	Intermediate Similarity	NPC269360
0.8065	Intermediate Similarity	NPC264005
0.8061	Intermediate Similarity	NPC473456
0.8058	Intermediate Similarity	NPC218123
0.8058	Intermediate Similarity	NPC112895
0.8058	Intermediate Similarity	NPC273155
0.8058	Intermediate Similarity	NPC231278
0.8041	Intermediate Similarity	NPC205173
0.8041	Intermediate Similarity	NPC266431
0.8022	Intermediate Similarity	NPC243347
0.8022	Intermediate Similarity	NPC118800
0.8021	Intermediate Similarity	NPC86368
0.8021	Intermediate Similarity	NPC214756
0.8021	Intermediate Similarity	NPC224060
0.8021	Intermediate Similarity	NPC473690
0.8021	Intermediate Similarity	NPC59170
0.8021	Intermediate Similarity	NPC287118
0.8021	Intermediate Similarity	NPC244356
0.8021	Intermediate Similarity	NPC471902
0.8021	Intermediate Similarity	NPC295643
0.8021	Intermediate Similarity	NPC272075
0.8021	Intermediate Similarity	NPC199543
0.802	Intermediate Similarity	NPC216114
0.802	Intermediate Similarity	NPC179208
0.8	Intermediate Similarity	NPC71706
0.8	Intermediate Similarity	NPC81530
0.8	Intermediate Similarity	NPC46441
0.8	Intermediate Similarity	NPC130278
0.8	Intermediate Similarity	NPC470281
0.8	Intermediate Similarity	NPC169933
0.8	Intermediate Similarity	NPC328264
0.8	Intermediate Similarity	NPC180849
0.7981	Intermediate Similarity	NPC2766
0.798	Intermediate Similarity	NPC474724
0.798	Intermediate Similarity	NPC260149
0.798	Intermediate Similarity	NPC58942
0.7979	Intermediate Similarity	NPC4309
0.7979	Intermediate Similarity	NPC472739
0.7979	Intermediate Similarity	NPC474925
0.7979	Intermediate Similarity	NPC56413
0.7979	Intermediate Similarity	NPC474719
0.7959	Intermediate Similarity	NPC305483
0.7959	Intermediate Similarity	NPC469545
0.7959	Intermediate Similarity	NPC96859
0.7959	Intermediate Similarity	NPC328162
0.7959	Intermediate Similarity	NPC476318
0.7959	Intermediate Similarity	NPC476327
0.7959	Intermediate Similarity	NPC264979
0.7959	Intermediate Similarity	NPC61369
0.7959	Intermediate Similarity	NPC256227
0.7959	Intermediate Similarity	NPC5532
0.7959	Intermediate Similarity	NPC157113
0.7959	Intermediate Similarity	NPC98874
0.7959	Intermediate Similarity	NPC62516
0.7959	Intermediate Similarity	NPC135548
0.7957	Intermediate Similarity	NPC98236
0.7957	Intermediate Similarity	NPC12774
0.7957	Intermediate Similarity	NPC269396
0.7957	Intermediate Similarity	NPC325594
0.7957	Intermediate Similarity	NPC2783
0.7957	Intermediate Similarity	NPC73038
0.7957	Intermediate Similarity	NPC187545
0.7955	Intermediate Similarity	NPC476811
0.7941	Intermediate Similarity	NPC29705
0.7941	Intermediate Similarity	NPC101842
0.7941	Intermediate Similarity	NPC84928
0.7941	Intermediate Similarity	NPC310586
0.7938	Intermediate Similarity	NPC222047
0.7938	Intermediate Similarity	NPC474529
0.7938	Intermediate Similarity	NPC74751
0.7921	Intermediate Similarity	NPC272472
0.7917	Intermediate Similarity	NPC158030
0.7917	Intermediate Similarity	NPC475416

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 NPC272635 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	2188
0.2-0.3	3811
0.3-0.4	1879
0.4-0.5	592
0.5-0.6	230
0.6-0.7	127
0.7-0.8	89
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD6881	Approved
0.8235	Intermediate Similarity	NPD6899	Approved
0.8218	Intermediate Similarity	NPD6402	Approved
0.8218	Intermediate Similarity	NPD6675	Approved
0.8218	Intermediate Similarity	NPD5739	Approved
0.8218	Intermediate Similarity	NPD7128	Approved
0.8137	Intermediate Similarity	NPD5697	Approved
0.8077	Intermediate Similarity	NPD7290	Approved
0.8077	Intermediate Similarity	NPD6883	Approved
0.8077	Intermediate Similarity	NPD7102	Approved
0.8058	Intermediate Similarity	NPD7320	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6649	Approved
0.8	Intermediate Similarity	NPD6847	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.7981	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD6372	Approved
0.7981	Intermediate Similarity	NPD6013	Approved
0.7981	Intermediate Similarity	NPD6014	Approved
0.7981	Intermediate Similarity	NPD6373	Approved
0.7961	Intermediate Similarity	NPD5701	Approved
0.7938	Intermediate Similarity	NPD7748	Approved
0.7925	Intermediate Similarity	NPD6882	Approved
0.7925	Intermediate Similarity	NPD8297	Approved
0.7917	Intermediate Similarity	NPD8035	Phase 2
0.7917	Intermediate Similarity	NPD7515	Phase 2
0.7917	Intermediate Similarity	NPD8034	Phase 2
0.7885	Intermediate Similarity	NPD6011	Approved
0.7879	Intermediate Similarity	NPD7902	Approved
0.7849	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4697	Phase 3
0.7723	Intermediate Similarity	NPD4696	Approved
0.7723	Intermediate Similarity	NPD5285	Approved
0.7723	Intermediate Similarity	NPD5286	Approved
0.77	Intermediate Similarity	NPD4755	Approved
0.7664	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5221	Approved
0.7576	Intermediate Similarity	NPD7900	Approved
0.7576	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5225	Approved
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7573	Intermediate Similarity	NPD5226	Approved
0.7573	Intermediate Similarity	NPD4633	Approved
0.7573	Intermediate Similarity	NPD5224	Approved
0.7551	Intermediate Similarity	NPD6079	Approved
0.7549	Intermediate Similarity	NPD4700	Approved
0.7547	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6274	Approved
0.7526	Intermediate Similarity	NPD5328	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7525	Intermediate Similarity	NPD6083	Phase 2
0.7525	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.7476	Intermediate Similarity	NPD5223	Approved
0.7475	Intermediate Similarity	NPD6399	Phase 3
0.7429	Intermediate Similarity	NPD5141	Approved
0.7411	Intermediate Similarity	NPD6335	Approved
0.7387	Intermediate Similarity	NPD6868	Approved
0.7364	Intermediate Similarity	NPD4632	Approved
0.7363	Intermediate Similarity	NPD6116	Phase 1
0.7321	Intermediate Similarity	NPD6317	Approved
0.732	Intermediate Similarity	NPD3573	Approved
0.7282	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD6319	Approved
0.7263	Intermediate Similarity	NPD4788	Approved
0.7257	Intermediate Similarity	NPD6313	Approved
0.7257	Intermediate Similarity	NPD6314	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7241	Intermediate Similarity	NPD8328	Phase 3
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD4730	Approved
0.7222	Intermediate Similarity	NPD4729	Approved
0.7217	Intermediate Similarity	NPD6909	Approved
0.7217	Intermediate Similarity	NPD6908	Approved
0.7216	Intermediate Similarity	NPD3618	Phase 1
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD4768	Approved
0.7196	Intermediate Similarity	NPD4767	Approved
0.7179	Intermediate Similarity	NPD7492	Approved
0.717	Intermediate Similarity	NPD4754	Approved
0.7168	Intermediate Similarity	NPD6009	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD6054	Approved
0.7119	Intermediate Similarity	NPD6616	Approved
0.7115	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7094	Intermediate Similarity	NPD7604	Phase 2
0.7091	Intermediate Similarity	NPD4634	Approved
0.7091	Intermediate Similarity	NPD5249	Phase 3
0.7091	Intermediate Similarity	NPD5247	Approved
0.7091	Intermediate Similarity	NPD5248	Approved
0.7091	Intermediate Similarity	NPD5251	Approved
0.7091	Intermediate Similarity	NPD5250	Approved
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5983	Phase 2
0.7069	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7078	Approved
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5216	Approved
0.7027	Intermediate Similarity	NPD5217	Approved
0.7027	Intermediate Similarity	NPD5215	Approved
0.7018	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4786	Approved
0.7009	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6101	Approved
0.6983	Remote Similarity	NPD6059	Approved
0.6979	Remote Similarity	NPD3667	Approved
0.6975	Remote Similarity	NPD6336	Discontinued
0.6975	Remote Similarity	NPD7507	Approved
0.6961	Remote Similarity	NPD4202	Approved
0.6957	Remote Similarity	NPD3703	Phase 2
0.6947	Remote Similarity	NPD4695	Discontinued
0.6937	Remote Similarity	NPD5135	Approved
0.6937	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5169	Approved
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD8293	Discontinued
0.6909	Remote Similarity	NPD5168	Approved
0.69	Remote Similarity	NPD6903	Approved
0.6881	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD5127	Approved
0.687	Remote Similarity	NPD7115	Discovery
0.6864	Remote Similarity	NPD5988	Approved
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7645	Phase 2
0.6837	Remote Similarity	NPD3666	Approved
0.6837	Remote Similarity	NPD3665	Phase 1
0.6837	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD6673	Approved
0.6832	Remote Similarity	NPD6904	Approved
0.6832	Remote Similarity	NPD6080	Approved
0.6827	Remote Similarity	NPD4629	Approved
0.6827	Remote Similarity	NPD5210	Approved
0.6813	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7319	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.678	Remote Similarity	NPD6921	Approved
0.6778	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7525	Registered
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD6686	Approved
0.6754	Remote Similarity	NPD8133	Approved
0.6703	Remote Similarity	NPD4789	Approved
0.67	Remote Similarity	NPD6098	Approved
0.67	Remote Similarity	NPD5279	Phase 3
0.6696	Remote Similarity	NPD5167	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD6435	Approved
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5777	Approved
0.6604	Remote Similarity	NPD7614	Phase 1
0.66	Remote Similarity	NPD5329	Approved
0.6562	Remote Similarity	NPD3617	Approved
0.6538	Remote Similarity	NPD5693	Phase 1
0.6538	Remote Similarity	NPD6050	Approved
0.6535	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4244	Approved
0.6522	Remote Similarity	NPD4245	Approved
0.6509	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3668	Phase 3
0.65	Remote Similarity	NPD4197	Approved
0.6491	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6081	Approved
0.6452	Remote Similarity	NPD6033	Approved
0.6449	Remote Similarity	NPD7732	Phase 3
0.6444	Remote Similarity	NPD4224	Phase 2
0.6442	Remote Similarity	NPD5692	Phase 3
0.6436	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD5368	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data