NPASS Compound

Structure

NPC164289 OpenBabel07101719252D 38 41 0 0 1 0 0 0 0 0999 V2000 5.1279 6.6371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4079 -0.1759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5381 0.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6398 2.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4079 -0.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2825 -1.8520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7949 1.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9203 0.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6160 5.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5917 1.0766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4371 1.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2633 -1.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9733 0.1004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0827 -1.5773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1279 3.2555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6160 2.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2341 -1.3426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1279 -0.3877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8603 -1.3247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8187 2.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5917 0.1004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8662 -0.5528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2825 1.0766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9733 1.0766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6143 -0.7586 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6160 4.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5892 -0.7076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1279 1.5647 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4371 -0.3877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2825 0.1004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8187 1.5647 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9114 -0.3498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6641 3.0290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5922 4.1009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1209 -1.5263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3068 0.7193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1279 4.9463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 5 29 1 0 0 0 0 9 37 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 32 1 0 0 0 0 20 31 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 12 1 6 0 0 0 22 32 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 28 1 6 0 0 0 24 31 1 0 0 0 0 25 27 1 6 0 0 0 25 38 1 0 0 0 0 26 34 2 0 0 0 0 26 37 1 0 0 0 0 27 35 1 0 0 0 0 28 4 1 6 0 0 0 29 30 1 6 0 0 0 30 6 1 6 0 0 0 31 7 1 6 0 0 0 31 36 1 0 0 0 0 32 8 1 1 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.41
Volume:	577.907
LogP:	4.779
LogD:	4.496
LogS:	-4.481
# Rotatable Bonds:	9
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	5.076
Fsp3:	0.969
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.029
MDCK Permeability:	3.7055317079648376e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.383

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	91.1612777709961%
Volume Distribution (VD):	0.798
Pgp-substrate:	2.3677990436553955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.318
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	4.252
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.246
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.934
Carcinogencity:	0.015
Eye Corrosion:	0.056
Eye Irritation:	0.175
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC164289

Natural Product ID:	NPC164289
*Common Name:**	Ethyl(4S,20S,24R)-Epoxy-4,25,29-Trihydroxy-3,4-Secodammar-3-Oate
IUPAC Name:	ethyl 3-[(3S,3aR,5aR,6R,7R,9aR,9bR)-7-[(2S)-1,2-dihydroxypropan-2-yl]-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:
Standard InCHIKey:	YESAZVXWVIEDQO-ALAXGYKUSA-N
Standard InCHI:	InChI=1S/C32H56O6/c1-9-37-26(34)15-16-28(4)23-11-10-21-22(32(8)19-14-25(38-32)27(2,3)35)12-17-29(21,5)30(23,6)18-13-24(28)31(7,36)20-33/h21-25,33,35-36H,9-20H2,1-8H3/t21-,22+,23-,24-,25-,28-,29-,30-,31-,32+/m1/s1
SMILES:	CCOC(=O)CC[C@]1(C)[C@H]2CC[C@@H]3[C@H](CC[C@@]3(C)[C@]2(C)CC[C@H]1[C@@](C)(CO)O)[C@]1(C)CC[C@H](C(C)(C)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109475
PubChem CID:	76310276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[568446]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[568446]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[568446]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[568446]

☑ 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 NPC164289 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	337
0.1-0.2	2912
0.2-0.3	11054
0.3-0.4	11959
0.4-0.5	5409
0.5-0.6	6992
0.6-0.7	3443
0.7-0.8	527
0.8-0.85	38
0.85-0.9	19
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100366
1.0	High Similarity	NPC311642
1.0	High Similarity	NPC242771
0.9487	High Similarity	NPC102156
0.9487	High Similarity	NPC148740
0.8929	High Similarity	NPC269267
0.8889	High Similarity	NPC217559
0.8889	High Similarity	NPC292458
0.8889	High Similarity	NPC268578
0.8861	High Similarity	NPC245029
0.8861	High Similarity	NPC31302
0.881	High Similarity	NPC48824
0.881	High Similarity	NPC229407
0.881	High Similarity	NPC250687
0.881	High Similarity	NPC254572
0.8795	High Similarity	NPC92139
0.8721	High Similarity	NPC471747
0.8659	High Similarity	NPC477285
0.8659	High Similarity	NPC111582
0.8642	High Similarity	NPC190940
0.8571	High Similarity	NPC80700
0.8571	High Similarity	NPC474448
0.8537	High Similarity	NPC477286
0.8537	High Similarity	NPC286719
0.8519	High Similarity	NPC472853
0.85	High Similarity	NPC199965
0.85	High Similarity	NPC476732
0.8471	Intermediate Similarity	NPC251808
0.8471	Intermediate Similarity	NPC474174
0.8462	Intermediate Similarity	NPC472944
0.8462	Intermediate Similarity	NPC472945
0.8434	Intermediate Similarity	NPC259173
0.8415	Intermediate Similarity	NPC58631
0.8395	Intermediate Similarity	NPC80891
0.8395	Intermediate Similarity	NPC201276
0.8375	Intermediate Similarity	NPC477919
0.8375	Intermediate Similarity	NPC180199
0.8372	Intermediate Similarity	NPC476435
0.8353	Intermediate Similarity	NPC114378
0.8353	Intermediate Similarity	NPC155531
0.8353	Intermediate Similarity	NPC215968
0.8353	Intermediate Similarity	NPC103782
0.8333	Intermediate Similarity	NPC116683
0.8315	Intermediate Similarity	NPC470424
0.8313	Intermediate Similarity	NPC477936
0.8313	Intermediate Similarity	NPC477935
0.8313	Intermediate Similarity	NPC121121
0.8272	Intermediate Similarity	NPC324700
0.8272	Intermediate Similarity	NPC34046
0.8272	Intermediate Similarity	NPC224802
0.8272	Intermediate Similarity	NPC80089
0.8272	Intermediate Similarity	NPC171426
0.8256	Intermediate Similarity	NPC239938
0.8205	Intermediate Similarity	NPC469940
0.8193	Intermediate Similarity	NPC12933
0.8161	Intermediate Similarity	NPC56777
0.8161	Intermediate Similarity	NPC201607
0.8161	Intermediate Similarity	NPC255176
0.8161	Intermediate Similarity	NPC471221
0.8161	Intermediate Similarity	NPC33398
0.814	Intermediate Similarity	NPC472745
0.814	Intermediate Similarity	NPC477283
0.814	Intermediate Similarity	NPC472272
0.8118	Intermediate Similarity	NPC471044
0.8118	Intermediate Similarity	NPC291310
0.8118	Intermediate Similarity	NPC473336
0.8111	Intermediate Similarity	NPC206878
0.8111	Intermediate Similarity	NPC470423
0.8077	Intermediate Similarity	NPC477929
0.8072	Intermediate Similarity	NPC261616
0.8025	Intermediate Similarity	NPC4209
0.8025	Intermediate Similarity	NPC477932
0.8025	Intermediate Similarity	NPC477933
0.8022	Intermediate Similarity	NPC215570
0.8	Intermediate Similarity	NPC280026
0.8	Intermediate Similarity	NPC472744
0.8	Intermediate Similarity	NPC167702
0.7978	Intermediate Similarity	NPC472146
0.7978	Intermediate Similarity	NPC470114
0.7978	Intermediate Similarity	NPC185529
0.7952	Intermediate Similarity	NPC220379
0.7952	Intermediate Similarity	NPC477287
0.7949	Intermediate Similarity	NPC252032
0.7949	Intermediate Similarity	NPC319671
0.7949	Intermediate Similarity	NPC469941
0.7949	Intermediate Similarity	NPC476734
0.7927	Intermediate Similarity	NPC477918
0.7927	Intermediate Similarity	NPC11907
0.7927	Intermediate Similarity	NPC474404
0.7927	Intermediate Similarity	NPC474574
0.7927	Intermediate Similarity	NPC207010
0.7927	Intermediate Similarity	NPC212453
0.7927	Intermediate Similarity	NPC64081
0.7927	Intermediate Similarity	NPC317913
0.7927	Intermediate Similarity	NPC264602
0.7927	Intermediate Similarity	NPC133596
0.7927	Intermediate Similarity	NPC171658
0.7907	Intermediate Similarity	NPC477434
0.7901	Intermediate Similarity	NPC270306
0.7901	Intermediate Similarity	NPC231680
0.7901	Intermediate Similarity	NPC212733
0.7901	Intermediate Similarity	NPC477934
0.7901	Intermediate Similarity	NPC91387
0.7889	Intermediate Similarity	NPC473066
0.7882	Intermediate Similarity	NPC154043
0.7882	Intermediate Similarity	NPC61107
0.7882	Intermediate Similarity	NPC289486
0.7882	Intermediate Similarity	NPC202688
0.7882	Intermediate Similarity	NPC60018
0.7872	Intermediate Similarity	NPC167974
0.7865	Intermediate Similarity	NPC200580
0.7865	Intermediate Similarity	NPC24705
0.7865	Intermediate Similarity	NPC56962
0.7857	Intermediate Similarity	NPC472943
0.7857	Intermediate Similarity	NPC470609
0.7857	Intermediate Similarity	NPC472951
0.7841	Intermediate Similarity	NPC202937
0.7831	Intermediate Similarity	NPC185465
0.7831	Intermediate Similarity	NPC471045
0.7816	Intermediate Similarity	NPC477445
0.7778	Intermediate Similarity	NPC472854
0.7778	Intermediate Similarity	NPC50443
0.7778	Intermediate Similarity	NPC18536
0.7778	Intermediate Similarity	NPC477930
0.7778	Intermediate Similarity	NPC55508
0.7765	Intermediate Similarity	NPC232625
0.7765	Intermediate Similarity	NPC77311
0.7765	Intermediate Similarity	NPC73515
0.7753	Intermediate Similarity	NPC476379
0.775	Intermediate Similarity	NPC197701
0.7742	Intermediate Similarity	NPC476728
0.7738	Intermediate Similarity	NPC320144
0.7738	Intermediate Similarity	NPC81074
0.7738	Intermediate Similarity	NPC477282
0.7732	Intermediate Similarity	NPC471293
0.7732	Intermediate Similarity	NPC100078
0.7727	Intermediate Similarity	NPC475007
0.7711	Intermediate Similarity	NPC143133
0.7711	Intermediate Similarity	NPC298168
0.7711	Intermediate Similarity	NPC471151
0.7711	Intermediate Similarity	NPC307865
0.7708	Intermediate Similarity	NPC213528
0.7708	Intermediate Similarity	NPC244969
0.7701	Intermediate Similarity	NPC65133
0.7701	Intermediate Similarity	NPC319909
0.7701	Intermediate Similarity	NPC473299
0.7701	Intermediate Similarity	NPC18953
0.7683	Intermediate Similarity	NPC24014
0.7683	Intermediate Similarity	NPC472311
0.7683	Intermediate Similarity	NPC186851
0.7683	Intermediate Similarity	NPC27349
0.7677	Intermediate Similarity	NPC224414
0.7674	Intermediate Similarity	NPC477446
0.7674	Intermediate Similarity	NPC477284
0.7674	Intermediate Similarity	NPC470155
0.7674	Intermediate Similarity	NPC477447
0.7674	Intermediate Similarity	NPC13494
0.7667	Intermediate Similarity	NPC61688
0.766	Intermediate Similarity	NPC253586
0.766	Intermediate Similarity	NPC472273
0.7653	Intermediate Similarity	NPC306776
0.7653	Intermediate Similarity	NPC166079
0.7647	Intermediate Similarity	NPC477851
0.7647	Intermediate Similarity	NPC170038
0.764	Intermediate Similarity	NPC5943
0.7634	Intermediate Similarity	NPC470031
0.7634	Intermediate Similarity	NPC279974
0.7625	Intermediate Similarity	NPC477850
0.7619	Intermediate Similarity	NPC252483
0.7619	Intermediate Similarity	NPC191345
0.7619	Intermediate Similarity	NPC329117
0.7614	Intermediate Similarity	NPC473350
0.7614	Intermediate Similarity	NPC476715
0.7614	Intermediate Similarity	NPC266651
0.7609	Intermediate Similarity	NPC256104
0.7609	Intermediate Similarity	NPC472232
0.7609	Intermediate Similarity	NPC211845
0.7609	Intermediate Similarity	NPC472238
0.7609	Intermediate Similarity	NPC182740
0.7609	Intermediate Similarity	NPC472237
0.7609	Intermediate Similarity	NPC472231
0.7609	Intermediate Similarity	NPC122083
0.759	Intermediate Similarity	NPC474020
0.7586	Intermediate Similarity	NPC470070
0.7586	Intermediate Similarity	NPC2572
0.7586	Intermediate Similarity	NPC29342
0.7582	Intermediate Similarity	NPC289213
0.7582	Intermediate Similarity	NPC77756
0.7579	Intermediate Similarity	NPC253995
0.7564	Intermediate Similarity	NPC42060
0.7564	Intermediate Similarity	NPC477931
0.7564	Intermediate Similarity	NPC268736
0.7558	Intermediate Similarity	NPC470156
0.7558	Intermediate Similarity	NPC280781
0.7558	Intermediate Similarity	NPC470154
0.7558	Intermediate Similarity	NPC48756
0.7558	Intermediate Similarity	NPC475743
0.7553	Intermediate Similarity	NPC475785
0.7553	Intermediate Similarity	NPC156377
0.7553	Intermediate Similarity	NPC237071

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 NPC164289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	3273
0.2-0.3	3646
0.3-0.4	1055
0.4-0.5	368
0.5-0.6	281
0.6-0.7	125
0.7-0.8	22
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
0.8272	Intermediate Similarity	NPD6115	Approved
0.8272	Intermediate Similarity	NPD6114	Approved
0.8272	Intermediate Similarity	NPD6118	Approved
0.8272	Intermediate Similarity	NPD6697	Approved
0.8025	Intermediate Similarity	NPD6117	Approved
0.8	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6116	Phase 1
0.7901	Intermediate Similarity	NPD3702	Approved
0.7662	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5777	Approved
0.7531	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6081	Approved
0.7407	Intermediate Similarity	NPD4245	Approved
0.7407	Intermediate Similarity	NPD4244	Approved
0.7407	Intermediate Similarity	NPD4789	Approved
0.7374	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4224	Phase 2
0.7284	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3698	Phase 2
0.7262	Intermediate Similarity	NPD3703	Phase 2
0.716	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5360	Phase 3
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7073	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.69	Remote Similarity	NPD1700	Approved
0.6875	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD7909	Approved
0.6875	Remote Similarity	NPD8171	Discontinued
0.6854	Remote Similarity	NPD6928	Phase 2
0.6822	Remote Similarity	NPD8133	Approved
0.68	Remote Similarity	NPD8418	Phase 2
0.6795	Remote Similarity	NPD3198	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6706	Remote Similarity	NPD4758	Discontinued
0.663	Remote Similarity	NPD4788	Approved
0.6629	Remote Similarity	NPD4238	Approved
0.6629	Remote Similarity	NPD5364	Discontinued
0.6629	Remote Similarity	NPD4802	Phase 2
0.6629	Remote Similarity	NPD3671	Phase 1
0.6579	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8297	Approved
0.6571	Remote Similarity	NPD6412	Phase 2
0.6559	Remote Similarity	NPD4786	Approved
0.6545	Remote Similarity	NPD6940	Discontinued
0.6535	Remote Similarity	NPD7638	Approved
0.6514	Remote Similarity	NPD4632	Approved
0.6509	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7320	Approved
0.6476	Remote Similarity	NPD5739	Approved
0.6476	Remote Similarity	NPD7128	Approved
0.6476	Remote Similarity	NPD6675	Approved
0.6476	Remote Similarity	NPD6402	Approved
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6458	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD5737	Approved
0.6449	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.641	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5695	Phase 3
0.6395	Remote Similarity	NPD4787	Phase 1
0.6381	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7492	Approved
0.6373	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD3730	Approved
0.6364	Remote Similarity	NPD3728	Approved
0.6356	Remote Similarity	NPD7736	Approved
0.6355	Remote Similarity	NPD6881	Approved
0.6355	Remote Similarity	NPD6686	Approved
0.6355	Remote Similarity	NPD6899	Approved
0.6354	Remote Similarity	NPD7524	Approved
0.6346	Remote Similarity	NPD7632	Discontinued
0.6344	Remote Similarity	NPD3667	Approved
0.6339	Remote Similarity	NPD7115	Discovery
0.633	Remote Similarity	NPD8130	Phase 1
0.6325	Remote Similarity	NPD6616	Approved
0.6325	Remote Similarity	NPD7507	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD6054	Approved
0.6316	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD6059	Approved
0.63	Remote Similarity	NPD7748	Approved
0.6296	Remote Similarity	NPD6372	Approved
0.6296	Remote Similarity	NPD6373	Approved
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3669	Approved
0.6277	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7078	Approved
0.6263	Remote Similarity	NPD7637	Suspended
0.6262	Remote Similarity	NPD5701	Approved
0.6262	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD6098	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6237	Remote Similarity	NPD1779	Approved
0.6237	Remote Similarity	NPD1780	Approved
0.6224	Remote Similarity	NPD6904	Approved
0.6224	Remote Similarity	NPD5328	Approved
0.6224	Remote Similarity	NPD6673	Approved
0.6224	Remote Similarity	NPD4753	Phase 2
0.6224	Remote Similarity	NPD6080	Approved
0.6211	Remote Similarity	NPD3666	Approved
0.6211	Remote Similarity	NPD3665	Phase 1
0.6211	Remote Similarity	NPD3133	Approved
0.6207	Remote Similarity	NPD6370	Approved
0.6204	Remote Similarity	NPD6011	Approved
0.6195	Remote Similarity	NPD6009	Approved
0.6182	Remote Similarity	NPD6617	Approved
0.6182	Remote Similarity	NPD6649	Approved
0.6182	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6650	Approved
0.6182	Remote Similarity	NPD6847	Approved
0.6182	Remote Similarity	NPD6869	Approved
0.6167	Remote Similarity	NPD7319	Approved
0.6154	Remote Similarity	NPD7604	Phase 2
0.6147	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6147	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6882	Approved
0.6121	Remote Similarity	NPD5983	Phase 2
0.6121	Remote Similarity	NPD6015	Approved
0.6121	Remote Similarity	NPD6016	Approved
0.6117	Remote Similarity	NPD7902	Approved
0.6105	Remote Similarity	NPD6695	Phase 3
0.61	Remote Similarity	NPD7515	Phase 2
0.61	Remote Similarity	NPD6079	Approved
0.6091	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3618	Phase 1
0.6078	Remote Similarity	NPD7991	Discontinued
0.6071	Remote Similarity	NPD371	Approved
0.6068	Remote Similarity	NPD5988	Approved
0.6058	Remote Similarity	NPD4225	Approved
0.6053	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6336	Discontinued
0.6044	Remote Similarity	NPD6933	Approved
0.6042	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4202	Approved
0.6034	Remote Similarity	NPD8377	Approved
0.6034	Remote Similarity	NPD8294	Approved
0.602	Remote Similarity	NPD7750	Discontinued
0.6019	Remote Similarity	NPD6920	Discontinued
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD7328	Approved
0.5983	Remote Similarity	NPD8380	Approved
0.5983	Remote Similarity	NPD8378	Approved
0.5983	Remote Similarity	NPD8296	Approved
0.5983	Remote Similarity	NPD8033	Approved
0.5983	Remote Similarity	NPD8379	Approved
0.5983	Remote Similarity	NPD8335	Approved
0.5982	Remote Similarity	NPD6053	Discontinued
0.598	Remote Similarity	NPD6001	Approved
0.5979	Remote Similarity	NPD5329	Approved
0.5977	Remote Similarity	NPD229	Approved
0.5977	Remote Similarity	NPD6705	Phase 1
0.5962	Remote Similarity	NPD4755	Approved
0.596	Remote Similarity	NPD5208	Approved
0.5957	Remote Similarity	NPD7525	Registered
0.595	Remote Similarity	NPD6033	Approved
0.5949	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7516	Approved
0.5946	Remote Similarity	NPD4634	Approved
0.5941	Remote Similarity	NPD6050	Approved
0.5941	Remote Similarity	NPD5693	Phase 1
0.5941	Remote Similarity	NPD5281	Approved
0.5941	Remote Similarity	NPD5284	Approved
0.5938	Remote Similarity	NPD5362	Discontinued
0.5929	Remote Similarity	NPD8298	Phase 2
0.5922	Remote Similarity	NPD4629	Approved
0.5922	Remote Similarity	NPD5210	Approved
0.5918	Remote Similarity	NPD5279	Phase 3
0.5914	Remote Similarity	NPD3617	Approved
0.5909	Remote Similarity	NPD3726	Approved
0.5909	Remote Similarity	NPD3725	Approved
0.59	Remote Similarity	NPD6051	Approved
0.5895	Remote Similarity	NPD4139	Approved
0.5895	Remote Similarity	NPD4692	Approved
0.5895	Remote Similarity	NPD5369	Approved
0.5882	Remote Similarity	NPD6067	Discontinued
0.5876	Remote Similarity	NPD4197	Approved
0.5876	Remote Similarity	NPD3668	Phase 3
0.5865	Remote Similarity	NPD5221	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