NPASS Compound

Structure

NPC26478 OpenBabel07101718182D 35 39 0 0 1 0 0 0 0 0999 V2000 -3.7536 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4442 1.6293 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 1.7321 -3.0000 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 0.8660 -2.5000 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 -3.9346 0.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 -5.3359 1.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3414 1.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 0.5181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 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 -0.9511 0.3090 0.0000 C 0 0 1 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 0.0000 -1.0000 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 -1.3578 1.2226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7426 2.5542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2533 2.2171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.3955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 8 10 1 0 0 0 0 8 19 2 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 13 29 1 0 0 0 0 14 27 1 0 0 0 0 15 24 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 31 1 0 0 0 0 18 12 1 1 0 0 0 18 35 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 30 1 6 0 0 0 21 14 1 1 0 0 0 21 25 1 0 0 0 0 21 35 1 0 0 0 0 22 27 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 6 0 0 0 24 30 1 0 0 0 0 24 33 2 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 34 1 0 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	4.338
LogD:	3.468
LogS:	-4.616
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.512
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.944
MDCK Permeability:	1.2633824553631712e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.854
30% Bioavailability (F30%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	77.44091033935547%
Volume Distribution (VD):	1.26
Pgp-substrate:	14.736893653869629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.135
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.634

ADMET: Excretion

Clearance (CL):	7.984
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.504
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.505
Carcinogencity:	0.278
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC26478

Natural Product ID:	NPC26478
*Common Name:**	Elaeocarpucin C
IUPAC Name:	n.a.
Synonyms:	Elaeocarpucin C
Standard InCHIKey:	IFEXLFRFNBMPPC-HHMFILIPSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-17(16-31)12-18-13-29(6,34)25-21(35-18)14-27(4)22-10-8-19-20(9-11-23(32)26(19,2)3)30(22,7)24(33)15-28(25,27)5/h8,12,18,20-23,25,31-32,34H,9-11,13-16H2,1-7H3/b17-12+/t18-,20+,21+,22-,23-,25-,27-,28+,29-,30-/m0/s1
SMILES:	OC/C(=C/[C@@H]1O[C@@H]2C[C@@]3([C@]([C@H]2[C@@](C1)(C)O)(C)CC(=O)[C@@]1([C@H]3CC=C2[C@H]1CC[C@@H](C2(C)C)O)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023378
PubChem CID:	57379696
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003059] 11-oxosteroids

*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
NPO32449	eleaocarpus chinensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22239601]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	410.0	nM	PMID[488875]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[488875]

☑ 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 NPC26478 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	201
0.1-0.2	1277
0.2-0.3	4193
0.3-0.4	9246
0.4-0.5	12424
0.5-0.6	6406
0.6-0.7	5701
0.7-0.8	3027
0.8-0.85	204
0.85-0.9	10
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC185530
0.9592	High Similarity	NPC60681
0.9495	High Similarity	NPC144459
0.94	High Similarity	NPC177064
0.9293	High Similarity	NPC149124
0.9293	High Similarity	NPC75531
0.9278	High Similarity	NPC83709
0.8911	High Similarity	NPC137657
0.88	High Similarity	NPC474327
0.8687	High Similarity	NPC126815
0.8673	High Similarity	NPC472932
0.8558	High Similarity	NPC185
0.8542	High Similarity	NPC2983
0.8529	High Similarity	NPC473424
0.8529	High Similarity	NPC87351
0.8529	High Similarity	NPC477915
0.8515	High Similarity	NPC473176
0.85	High Similarity	NPC190554
0.85	High Similarity	NPC291634
0.8485	Intermediate Similarity	NPC469599
0.8469	Intermediate Similarity	NPC472930
0.8469	Intermediate Similarity	NPC472942
0.8462	Intermediate Similarity	NPC149047
0.8454	Intermediate Similarity	NPC48010
0.8454	Intermediate Similarity	NPC320026
0.8447	Intermediate Similarity	NPC311612
0.8431	Intermediate Similarity	NPC476897
0.8431	Intermediate Similarity	NPC473174
0.8421	Intermediate Similarity	NPC469994
0.8416	Intermediate Similarity	NPC303777
0.8416	Intermediate Similarity	NPC471784
0.84	Intermediate Similarity	NPC249954
0.84	Intermediate Similarity	NPC160056
0.8396	Intermediate Similarity	NPC214644
0.8384	Intermediate Similarity	NPC292793
0.8381	Intermediate Similarity	NPC475060
0.8381	Intermediate Similarity	NPC83744
0.8381	Intermediate Similarity	NPC477916
0.8381	Intermediate Similarity	NPC220229
0.8378	Intermediate Similarity	NPC475041
0.8365	Intermediate Similarity	NPC209502
0.8365	Intermediate Similarity	NPC204833
0.8351	Intermediate Similarity	NPC474245
0.8351	Intermediate Similarity	NPC76879
0.8351	Intermediate Similarity	NPC32830
0.8351	Intermediate Similarity	NPC31985
0.8351	Intermediate Similarity	NPC1015
0.835	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC149224
0.8333	Intermediate Similarity	NPC477521
0.8333	Intermediate Similarity	NPC317590
0.8333	Intermediate Similarity	NPC207251
0.8333	Intermediate Similarity	NPC154072
0.8333	Intermediate Similarity	NPC100267
0.8333	Intermediate Similarity	NPC475524
0.8333	Intermediate Similarity	NPC15390
0.8318	Intermediate Similarity	NPC76084
0.8317	Intermediate Similarity	NPC18509
0.8317	Intermediate Similarity	NPC107243
0.8317	Intermediate Similarity	NPC475894
0.8316	Intermediate Similarity	NPC471224
0.8316	Intermediate Similarity	NPC266511
0.8302	Intermediate Similarity	NPC217201
0.8302	Intermediate Similarity	NPC329417
0.83	Intermediate Similarity	NPC259286
0.8288	Intermediate Similarity	NPC329736
0.8288	Intermediate Similarity	NPC311554
0.8288	Intermediate Similarity	NPC257457
0.8286	Intermediate Similarity	NPC49958
0.8286	Intermediate Similarity	NPC260268
0.8286	Intermediate Similarity	NPC50692
0.8286	Intermediate Similarity	NPC302607
0.8286	Intermediate Similarity	NPC231530
0.8286	Intermediate Similarity	NPC478052
0.8286	Intermediate Similarity	NPC476027
0.8286	Intermediate Similarity	NPC152695
0.8286	Intermediate Similarity	NPC48733
0.8286	Intermediate Similarity	NPC202167
0.8286	Intermediate Similarity	NPC296945
0.8286	Intermediate Similarity	NPC85829
0.8286	Intermediate Similarity	NPC150531
0.8286	Intermediate Similarity	NPC214264
0.8286	Intermediate Similarity	NPC319077
0.8286	Intermediate Similarity	NPC257353
0.8286	Intermediate Similarity	NPC97202
0.8286	Intermediate Similarity	NPC278628
0.8286	Intermediate Similarity	NPC171137
0.8283	Intermediate Similarity	NPC69454
0.8283	Intermediate Similarity	NPC477520
0.8273	Intermediate Similarity	NPC148458
0.8269	Intermediate Similarity	NPC111323
0.8269	Intermediate Similarity	NPC191892
0.8269	Intermediate Similarity	NPC236390
0.8265	Intermediate Similarity	NPC69622
0.8265	Intermediate Similarity	NPC171441
0.8257	Intermediate Similarity	NPC317210
0.8257	Intermediate Similarity	NPC122056
0.8252	Intermediate Similarity	NPC81530
0.8247	Intermediate Similarity	NPC328313
0.8247	Intermediate Similarity	NPC53911
0.8235	Intermediate Similarity	NPC477854
0.8235	Intermediate Similarity	NPC197386
0.8224	Intermediate Similarity	NPC11710
0.8218	Intermediate Similarity	NPC78473
0.8218	Intermediate Similarity	NPC49371
0.8218	Intermediate Similarity	NPC471463
0.8218	Intermediate Similarity	NPC328371
0.8214	Intermediate Similarity	NPC61520
0.8214	Intermediate Similarity	NPC264954
0.8214	Intermediate Similarity	NPC473270
0.8211	Intermediate Similarity	NPC221758
0.8211	Intermediate Similarity	NPC59453
0.8211	Intermediate Similarity	NPC82902
0.8208	Intermediate Similarity	NPC475294
0.82	Intermediate Similarity	NPC8993
0.8198	Intermediate Similarity	NPC471854
0.8198	Intermediate Similarity	NPC470959
0.8198	Intermediate Similarity	NPC476965
0.8182	Intermediate Similarity	NPC67259
0.8182	Intermediate Similarity	NPC472975
0.8182	Intermediate Similarity	NPC473998
0.8182	Intermediate Similarity	NPC326542
0.8182	Intermediate Similarity	NPC472978
0.8182	Intermediate Similarity	NPC147912
0.8182	Intermediate Similarity	NPC475806
0.8182	Intermediate Similarity	NPC63748
0.8173	Intermediate Similarity	NPC195290
0.8173	Intermediate Similarity	NPC473928
0.8173	Intermediate Similarity	NPC204450
0.8165	Intermediate Similarity	NPC191620
0.8165	Intermediate Similarity	NPC221144
0.8165	Intermediate Similarity	NPC126691
0.8165	Intermediate Similarity	NPC476163
0.8163	Intermediate Similarity	NPC472970
0.8163	Intermediate Similarity	NPC473999
0.8163	Intermediate Similarity	NPC472971
0.8163	Intermediate Similarity	NPC477943
0.8163	Intermediate Similarity	NPC309603
0.8158	Intermediate Similarity	NPC269642
0.8155	Intermediate Similarity	NPC144956
0.8155	Intermediate Similarity	NPC218383
0.8155	Intermediate Similarity	NPC110149
0.8148	Intermediate Similarity	NPC37116
0.8144	Intermediate Similarity	NPC475740
0.8144	Intermediate Similarity	NPC90652
0.8142	Intermediate Similarity	NPC476962
0.8142	Intermediate Similarity	NPC474370
0.8137	Intermediate Similarity	NPC253826
0.8137	Intermediate Similarity	NPC57416
0.8137	Intermediate Similarity	NPC18319
0.8137	Intermediate Similarity	NPC254496
0.8137	Intermediate Similarity	NPC151488
0.8131	Intermediate Similarity	NPC94529
0.8131	Intermediate Similarity	NPC65941
0.8125	Intermediate Similarity	NPC274448
0.8125	Intermediate Similarity	NPC474083
0.8125	Intermediate Similarity	NPC474218
0.8119	Intermediate Similarity	NPC173875
0.8119	Intermediate Similarity	NPC469995
0.8119	Intermediate Similarity	NPC271195
0.8119	Intermediate Similarity	NPC174948
0.8119	Intermediate Similarity	NPC473170
0.8119	Intermediate Similarity	NPC318282
0.8108	Intermediate Similarity	NPC270929
0.8105	Intermediate Similarity	NPC278648
0.8105	Intermediate Similarity	NPC470047
0.8105	Intermediate Similarity	NPC476082
0.8105	Intermediate Similarity	NPC470046
0.8095	Intermediate Similarity	NPC324001
0.8095	Intermediate Similarity	NPC112009
0.8095	Intermediate Similarity	NPC36688
0.8095	Intermediate Similarity	NPC247957
0.8095	Intermediate Similarity	NPC249187
0.8095	Intermediate Similarity	NPC90177
0.8091	Intermediate Similarity	NPC73300
0.8091	Intermediate Similarity	NPC108721
0.8091	Intermediate Similarity	NPC250109
0.8091	Intermediate Similarity	NPC962
0.8087	Intermediate Similarity	NPC473979
0.8087	Intermediate Similarity	NPC204812
0.8073	Intermediate Similarity	NPC474315
0.8073	Intermediate Similarity	NPC43775
0.807	Intermediate Similarity	NPC46570
0.807	Intermediate Similarity	NPC473256
0.807	Intermediate Similarity	NPC470878
0.8061	Intermediate Similarity	NPC470417
0.8061	Intermediate Similarity	NPC328539
0.8061	Intermediate Similarity	NPC471952
0.8058	Intermediate Similarity	NPC176845
0.8056	Intermediate Similarity	NPC472216
0.8056	Intermediate Similarity	NPC284828
0.8056	Intermediate Similarity	NPC173905
0.8056	Intermediate Similarity	NPC5475
0.8053	Intermediate Similarity	NPC476960
0.8041	Intermediate Similarity	NPC51014
0.8041	Intermediate Similarity	NPC474733
0.8041	Intermediate Similarity	NPC293287
0.8041	Intermediate Similarity	NPC474778
0.8041	Intermediate Similarity	NPC470051
0.8041	Intermediate Similarity	NPC31564

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 NPC26478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1484
0.2-0.3	3773
0.3-0.4	2455
0.4-0.5	749
0.5-0.6	176
0.6-0.7	188
0.7-0.8	140
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.835	Intermediate Similarity	NPD5211	Phase 2
0.8317	Intermediate Similarity	NPD4755	Approved
0.8286	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD6675	Approved
0.8286	Intermediate Similarity	NPD7128	Approved
0.8286	Intermediate Similarity	NPD5739	Approved
0.8211	Intermediate Similarity	NPD4786	Approved
0.819	Intermediate Similarity	NPD5141	Approved
0.8163	Intermediate Similarity	NPD5328	Approved
0.8155	Intermediate Similarity	NPD4696	Approved
0.8155	Intermediate Similarity	NPD4700	Approved
0.8155	Intermediate Similarity	NPD5286	Approved
0.8155	Intermediate Similarity	NPD5285	Approved
0.8131	Intermediate Similarity	NPD7320	Approved
0.8131	Intermediate Similarity	NPD6899	Approved
0.8131	Intermediate Similarity	NPD6881	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8037	Intermediate Similarity	NPD5697	Approved
0.8037	Intermediate Similarity	NPD5701	Approved
0.8036	Intermediate Similarity	NPD7115	Discovery
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD5226	Approved
0.8	Intermediate Similarity	NPD5225	Approved
0.8	Intermediate Similarity	NPD4633	Approved
0.8	Intermediate Similarity	NPD5224	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.798	Intermediate Similarity	NPD4753	Phase 2
0.7961	Intermediate Similarity	NPD6083	Phase 2
0.7961	Intermediate Similarity	NPD6084	Phase 2
0.7925	Intermediate Similarity	NPD5175	Approved
0.7925	Intermediate Similarity	NPD5174	Approved
0.7921	Intermediate Similarity	NPD4202	Approved
0.7921	Intermediate Similarity	NPD6399	Phase 3
0.7909	Intermediate Similarity	NPD6617	Approved
0.7909	Intermediate Similarity	NPD6869	Approved
0.7909	Intermediate Similarity	NPD6649	Approved
0.7909	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD6650	Approved
0.7909	Intermediate Similarity	NPD8130	Phase 1
0.7905	Intermediate Similarity	NPD5223	Approved
0.789	Intermediate Similarity	NPD6013	Approved
0.789	Intermediate Similarity	NPD6012	Approved
0.789	Intermediate Similarity	NPD6014	Approved
0.7838	Intermediate Similarity	NPD8297	Approved
0.7838	Intermediate Similarity	NPD6882	Approved
0.7835	Intermediate Similarity	NPD3666	Approved
0.7835	Intermediate Similarity	NPD3133	Approved
0.7835	Intermediate Similarity	NPD3665	Phase 1
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.7798	Intermediate Similarity	NPD6011	Approved
0.7778	Intermediate Similarity	NPD4768	Approved
0.7778	Intermediate Similarity	NPD4767	Approved
0.7757	Intermediate Similarity	NPD4754	Approved
0.7748	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD4697	Phase 3
0.7692	Intermediate Similarity	NPD5221	Approved
0.7692	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5222	Approved
0.7677	Intermediate Similarity	NPD3618	Phase 1
0.7647	Intermediate Similarity	NPD7507	Approved
0.7636	Intermediate Similarity	NPD4729	Approved
0.7636	Intermediate Similarity	NPD4730	Approved
0.7636	Intermediate Similarity	NPD5128	Approved
0.7629	Intermediate Similarity	NPD4221	Approved
0.7629	Intermediate Similarity	NPD4223	Phase 3
0.7619	Intermediate Similarity	NPD5173	Approved
0.7596	Intermediate Similarity	NPD4629	Approved
0.7596	Intermediate Similarity	NPD5210	Approved
0.7596	Intermediate Similarity	NPD5695	Phase 3
0.7576	Intermediate Similarity	NPD5329	Approved
0.7547	Intermediate Similarity	NPD5696	Approved
0.7545	Intermediate Similarity	NPD6412	Phase 2
0.7525	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD5247	Approved
0.75	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD5251	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD5249	Phase 3
0.75	Intermediate Similarity	NPD5248	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7478	Intermediate Similarity	NPD6274	Approved
0.7476	Intermediate Similarity	NPD5693	Phase 1
0.7475	Intermediate Similarity	NPD3668	Phase 3
0.7475	Intermediate Similarity	NPD4197	Approved
0.7459	Intermediate Similarity	NPD7319	Approved
0.7455	Intermediate Similarity	NPD6008	Approved
0.7451	Intermediate Similarity	NPD6051	Approved
0.7436	Intermediate Similarity	NPD7100	Approved
0.7436	Intermediate Similarity	NPD7101	Approved
0.7434	Intermediate Similarity	NPD5216	Approved
0.7434	Intermediate Similarity	NPD5215	Approved
0.7434	Intermediate Similarity	NPD5217	Approved
0.7426	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4788	Approved
0.7373	Intermediate Similarity	NPD6059	Approved
0.7373	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6903	Approved
0.735	Intermediate Similarity	NPD6335	Approved
0.7345	Intermediate Similarity	NPD5135	Approved
0.7345	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5169	Approved
0.7333	Intermediate Similarity	NPD7748	Approved
0.7327	Intermediate Similarity	NPD4138	Approved
0.7327	Intermediate Similarity	NPD6098	Approved
0.7327	Intermediate Similarity	NPD4688	Approved
0.7327	Intermediate Similarity	NPD4690	Approved
0.7327	Intermediate Similarity	NPD4693	Phase 3
0.7327	Intermediate Similarity	NPD4689	Approved
0.7327	Intermediate Similarity	NPD5205	Approved
0.7311	Intermediate Similarity	NPD6908	Approved
0.7311	Intermediate Similarity	NPD6909	Approved
0.7308	Intermediate Similarity	NPD7515	Phase 2
0.7304	Intermediate Similarity	NPD4632	Approved
0.7282	Intermediate Similarity	NPD6904	Approved
0.7282	Intermediate Similarity	NPD6080	Approved
0.7282	Intermediate Similarity	NPD6673	Approved
0.7281	Intermediate Similarity	NPD5127	Approved
0.7265	Intermediate Similarity	NPD6317	Approved
0.7264	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7339	Approved
0.7263	Intermediate Similarity	NPD6942	Approved
0.725	Intermediate Similarity	NPD6370	Approved
0.7245	Intermediate Similarity	NPD7525	Registered
0.7228	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6319	Approved
0.7203	Intermediate Similarity	NPD6313	Approved
0.7203	Intermediate Similarity	NPD6314	Approved
0.72	Intermediate Similarity	NPD6695	Phase 3
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7182	Intermediate Similarity	NPD7632	Discontinued
0.7167	Intermediate Similarity	NPD6016	Approved
0.7167	Intermediate Similarity	NPD6015	Approved
0.7157	Intermediate Similarity	NPD4694	Approved
0.7157	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5280	Approved
0.7157	Intermediate Similarity	NPD5690	Phase 2
0.7157	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7131	Intermediate Similarity	NPD7492	Approved
0.713	Intermediate Similarity	NPD7902	Approved
0.7129	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6009	Approved
0.7107	Intermediate Similarity	NPD5988	Approved
0.7097	Intermediate Similarity	NPD7736	Approved
0.7094	Intermediate Similarity	NPD5167	Approved
0.7087	Intermediate Similarity	NPD3573	Approved
0.7073	Intermediate Similarity	NPD6616	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD7327	Approved
0.7049	Intermediate Similarity	NPD7604	Phase 2
0.7048	Intermediate Similarity	NPD5785	Approved
0.7034	Intermediate Similarity	NPD6868	Approved
0.703	Intermediate Similarity	NPD5362	Discontinued
0.7025	Intermediate Similarity	NPD8033	Approved
0.7025	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5983	Phase 2
0.7019	Intermediate Similarity	NPD5208	Approved
0.7018	Intermediate Similarity	NPD5168	Approved
0.7016	Intermediate Similarity	NPD7078	Approved
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.699	Remote Similarity	NPD5786	Approved
0.699	Remote Similarity	NPD4519	Discontinued
0.699	Remote Similarity	NPD4623	Approved
0.6981	Remote Similarity	NPD5284	Approved
0.6981	Remote Similarity	NPD6050	Approved
0.6981	Remote Similarity	NPD5281	Approved
0.6981	Remote Similarity	NPD7637	Suspended
0.6979	Remote Similarity	NPD4785	Approved
0.6979	Remote Similarity	NPD4784	Approved
0.697	Remote Similarity	NPD4195	Approved
0.697	Remote Similarity	NPD7645	Phase 2
0.6952	Remote Similarity	NPD6101	Approved
0.6952	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4243	Approved
0.6942	Remote Similarity	NPD8294	Approved
0.6942	Remote Similarity	NPD8377	Approved
0.6935	Remote Similarity	NPD6336	Discontinued
0.6931	Remote Similarity	NPD6435	Approved
0.6923	Remote Similarity	NPD7524	Approved
0.6923	Remote Similarity	NPD7750	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