NPASS Compound

Structure

NPC75531 OpenBabel07101719252D 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 -5.3359 1.6407 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 -0.9511 -1.3090 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 0.8660 0.5000 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 2.5981 -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 -2.9401 0.5181 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 -3.9346 0.6226 0.0000 C 0 0 1 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 5.1962 -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 -4.5224 -0.1864 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 16 2 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 29 1 0 0 0 0 15 23 1 0 0 0 0 15 28 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 30 1 6 0 0 0 19 24 1 1 0 0 0 19 35 1 0 0 0 0 20 13 1 1 0 0 0 20 25 1 0 0 0 0 20 35 1 0 0 0 0 21 27 1 1 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 1 6 0 0 0 23 30 1 0 0 0 0 23 32 2 0 0 0 0 24 33 1 1 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 6 1 6 0 0 0 29 7 1 1 0 0 0 29 34 1 0 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	4.527
LogD:	3.594
LogS:	-4.622
# 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:	5.567
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:	-4.923
MDCK Permeability:	1.2392480130074546e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.629
Plasma Protein Binding (PPB):	67.44093322753906%
Volume Distribution (VD):	1.537
Pgp-substrate:	20.94966697692871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.544

ADMET: Excretion

Clearance (CL):	10.325
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.282
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.185
Carcinogencity:	0.701
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC75531

Natural Product ID:	NPC75531
*Common Name:**	Elaeocarpucin A
IUPAC Name:	n.a.
Synonyms:	Elaeocarpucin A
Standard InCHIKey:	JRJRXOXXSPJQTA-ZFMNZAKFSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-16(2)24(33)19-14-29(7,34)25-20(35-19)13-27(5)21-11-9-17-18(10-12-22(31)26(17,3)4)30(21,8)23(32)15-28(25,27)6/h9,18-22,24-25,31,33-34H,1,10-15H2,2-8H3/t18-,19-,20-,21+,22+,24+,25+,27+,28-,29+,30+/m1/s1
SMILES:	CC(=C)[C@@H]([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)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023376
PubChem CID:	57379694
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	>	10000.0	nM	PMID[455608]

☑ 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 NPC75531 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	204
0.1-0.2	1271
0.2-0.3	4387
0.3-0.4	9919
0.4-0.5	11749
0.5-0.6	6117
0.6-0.7	5345
0.7-0.8	3463
0.8-0.85	214
0.85-0.9	19
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC149124
0.9596	High Similarity	NPC144459
0.9293	High Similarity	NPC26478
0.9192	High Similarity	NPC185530
0.9184	High Similarity	NPC83709
0.8922	High Similarity	NPC60681
0.8824	High Similarity	NPC137657
0.8812	High Similarity	NPC473928
0.8774	High Similarity	NPC207251
0.875	High Similarity	NPC177064
0.8713	High Similarity	NPC476897
0.8692	High Similarity	NPC317210
0.8673	High Similarity	NPC174051
0.8673	High Similarity	NPC67831
0.8654	High Similarity	NPC475060
0.8654	High Similarity	NPC83744
0.8654	High Similarity	NPC220229
0.8646	High Similarity	NPC32830
0.8636	High Similarity	NPC61520
0.8627	High Similarity	NPC477915
0.8627	High Similarity	NPC473424
0.8611	High Similarity	NPC326542
0.86	High Similarity	NPC190554
0.8571	High Similarity	NPC217201
0.8571	High Similarity	NPC329417
0.8558	High Similarity	NPC49958
0.8558	High Similarity	NPC97202
0.8558	High Similarity	NPC302607
0.8558	High Similarity	NPC202167
0.8558	High Similarity	NPC214264
0.8558	High Similarity	NPC150531
0.8558	High Similarity	NPC149047
0.8558	High Similarity	NPC171137
0.8558	High Similarity	NPC152695
0.8558	High Similarity	NPC296945
0.8558	High Similarity	NPC260268
0.8558	High Similarity	NPC476027
0.8558	High Similarity	NPC48733
0.8558	High Similarity	NPC50692
0.8558	High Similarity	NPC85829
0.8558	High Similarity	NPC319077
0.8545	High Similarity	NPC329736
0.8544	High Similarity	NPC191892
0.8542	High Similarity	NPC470417
0.8529	High Similarity	NPC474327
0.8519	High Similarity	NPC194100
0.8519	High Similarity	NPC250109
0.8491	Intermediate Similarity	NPC11710
0.8491	Intermediate Similarity	NPC41405
0.8491	Intermediate Similarity	NPC214644
0.8476	Intermediate Similarity	NPC477916
0.8469	Intermediate Similarity	NPC262870
0.8468	Intermediate Similarity	NPC475041
0.8462	Intermediate Similarity	NPC209502
0.8462	Intermediate Similarity	NPC204833
0.8438	Intermediate Similarity	NPC90652
0.8431	Intermediate Similarity	NPC473176
0.8431	Intermediate Similarity	NPC15390
0.8431	Intermediate Similarity	NPC110149
0.8416	Intermediate Similarity	NPC18509
0.8411	Intermediate Similarity	NPC52241
0.8411	Intermediate Similarity	NPC76084
0.8411	Intermediate Similarity	NPC154856
0.8411	Intermediate Similarity	NPC475317
0.8407	Intermediate Similarity	NPC28532
0.84	Intermediate Similarity	NPC473170
0.84	Intermediate Similarity	NPC472932
0.84	Intermediate Similarity	NPC469599
0.8396	Intermediate Similarity	NPC65941
0.8381	Intermediate Similarity	NPC278628
0.8381	Intermediate Similarity	NPC231530
0.8367	Intermediate Similarity	NPC171441
0.8364	Intermediate Similarity	NPC270929
0.835	Intermediate Similarity	NPC473174
0.8349	Intermediate Similarity	NPC108721
0.8349	Intermediate Similarity	NPC962
0.8349	Intermediate Similarity	NPC178981
0.8349	Intermediate Similarity	NPC73300
0.8333	Intermediate Similarity	NPC469994
0.8333	Intermediate Similarity	NPC471784
0.8333	Intermediate Similarity	NPC303777
0.8317	Intermediate Similarity	NPC471463
0.8302	Intermediate Similarity	NPC165873
0.8302	Intermediate Similarity	NPC185
0.8302	Intermediate Similarity	NPC59530
0.8288	Intermediate Similarity	NPC471854
0.8286	Intermediate Similarity	NPC471293
0.8269	Intermediate Similarity	NPC136289
0.8269	Intermediate Similarity	NPC87351
0.8265	Intermediate Similarity	NPC31985
0.8265	Intermediate Similarity	NPC1015
0.8265	Intermediate Similarity	NPC2983
0.8265	Intermediate Similarity	NPC76879
0.8265	Intermediate Similarity	NPC474245
0.8257	Intermediate Similarity	NPC130427
0.8257	Intermediate Similarity	NPC280782
0.8257	Intermediate Similarity	NPC474265
0.8257	Intermediate Similarity	NPC210420
0.8252	Intermediate Similarity	NPC218383
0.8252	Intermediate Similarity	NPC154072
0.8252	Intermediate Similarity	NPC144956
0.8252	Intermediate Similarity	NPC167974
0.8247	Intermediate Similarity	NPC317590
0.8246	Intermediate Similarity	NPC269642
0.8235	Intermediate Similarity	NPC107243
0.823	Intermediate Similarity	NPC474370
0.823	Intermediate Similarity	NPC472257
0.8224	Intermediate Similarity	NPC472218
0.8224	Intermediate Similarity	NPC472217
0.8224	Intermediate Similarity	NPC94529
0.8224	Intermediate Similarity	NPC472219
0.8208	Intermediate Similarity	NPC210178
0.82	Intermediate Similarity	NPC472930
0.82	Intermediate Similarity	NPC472942
0.82	Intermediate Similarity	NPC472496
0.8198	Intermediate Similarity	NPC266728
0.8198	Intermediate Similarity	NPC49492
0.819	Intermediate Similarity	NPC236390
0.819	Intermediate Similarity	NPC239716
0.819	Intermediate Similarity	NPC311612
0.819	Intermediate Similarity	NPC117185
0.8182	Intermediate Similarity	NPC260665
0.8182	Intermediate Similarity	NPC48010
0.8182	Intermediate Similarity	NPC255017
0.8182	Intermediate Similarity	NPC320026
0.8174	Intermediate Similarity	NPC473979
0.8173	Intermediate Similarity	NPC81530
0.8165	Intermediate Similarity	NPC471243
0.8163	Intermediate Similarity	NPC328313
0.8163	Intermediate Similarity	NPC53911
0.8158	Intermediate Similarity	NPC46570
0.8155	Intermediate Similarity	NPC477854
0.8148	Intermediate Similarity	NPC246205
0.8148	Intermediate Similarity	NPC173905
0.8148	Intermediate Similarity	NPC5475
0.8148	Intermediate Similarity	NPC143706
0.8148	Intermediate Similarity	NPC284828
0.8148	Intermediate Similarity	NPC472534
0.8148	Intermediate Similarity	NPC472216
0.8142	Intermediate Similarity	NPC264954
0.8142	Intermediate Similarity	NPC161738
0.8137	Intermediate Similarity	NPC49371
0.8137	Intermediate Similarity	NPC249954
0.8131	Intermediate Similarity	NPC44063
0.8125	Intermediate Similarity	NPC82902
0.8125	Intermediate Similarity	NPC221758
0.8125	Intermediate Similarity	NPC470959
0.8125	Intermediate Similarity	NPC476965
0.8125	Intermediate Similarity	NPC218970
0.8125	Intermediate Similarity	NPC470171
0.8125	Intermediate Similarity	NPC59453
0.812	Intermediate Similarity	NPC473265
0.812	Intermediate Similarity	NPC470882
0.812	Intermediate Similarity	NPC473253
0.8119	Intermediate Similarity	NPC240617
0.8119	Intermediate Similarity	NPC292793
0.8119	Intermediate Similarity	NPC472976
0.8119	Intermediate Similarity	NPC472977
0.8119	Intermediate Similarity	NPC111015
0.8108	Intermediate Similarity	NPC473898
0.8108	Intermediate Similarity	NPC473882
0.8108	Intermediate Similarity	NPC243354
0.8108	Intermediate Similarity	NPC477580
0.8108	Intermediate Similarity	NPC474557
0.8103	Intermediate Similarity	NPC475194
0.81	Intermediate Similarity	NPC155304
0.81	Intermediate Similarity	NPC473166
0.81	Intermediate Similarity	NPC154101
0.8095	Intermediate Similarity	NPC195290
0.8095	Intermediate Similarity	NPC22388
0.8095	Intermediate Similarity	NPC204450
0.8091	Intermediate Similarity	NPC191620
0.8091	Intermediate Similarity	NPC126691
0.8087	Intermediate Similarity	NPC88326
0.8087	Intermediate Similarity	NPC153700
0.8087	Intermediate Similarity	NPC222688
0.8087	Intermediate Similarity	NPC107493
0.8081	Intermediate Similarity	NPC476733
0.8081	Intermediate Similarity	NPC477943
0.8081	Intermediate Similarity	NPC229871
0.8081	Intermediate Similarity	NPC215029
0.8081	Intermediate Similarity	NPC469319
0.8077	Intermediate Similarity	NPC477521
0.8073	Intermediate Similarity	NPC197428
0.8073	Intermediate Similarity	NPC37116
0.807	Intermediate Similarity	NPC471406
0.807	Intermediate Similarity	NPC79579
0.8061	Intermediate Similarity	NPC475740
0.8058	Intermediate Similarity	NPC57416
0.8058	Intermediate Similarity	NPC18319
0.8058	Intermediate Similarity	NPC475894
0.8058	Intermediate Similarity	NPC474785
0.8058	Intermediate Similarity	NPC474938
0.8058	Intermediate Similarity	NPC126815
0.8056	Intermediate Similarity	NPC295389
0.8053	Intermediate Similarity	NPC257457
0.8053	Intermediate Similarity	NPC153440
0.8053	Intermediate Similarity	NPC311554
0.8053	Intermediate Similarity	NPC86020
0.8053	Intermediate Similarity	NPC50774

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 NPC75531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1525
0.2-0.3	3935
0.3-0.4	2361
0.4-0.5	648
0.5-0.6	183
0.6-0.7	162
0.7-0.8	141
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8447	Intermediate Similarity	NPD5211	Phase 2
0.8416	Intermediate Similarity	NPD4755	Approved
0.8381	Intermediate Similarity	NPD6675	Approved
0.8381	Intermediate Similarity	NPD7128	Approved
0.8381	Intermediate Similarity	NPD5739	Approved
0.8381	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD5141	Approved
0.8257	Intermediate Similarity	NPD8297	Approved
0.8252	Intermediate Similarity	NPD4700	Approved
0.8252	Intermediate Similarity	NPD4696	Approved
0.8252	Intermediate Similarity	NPD5286	Approved
0.8252	Intermediate Similarity	NPD5285	Approved
0.8224	Intermediate Similarity	NPD6899	Approved
0.8224	Intermediate Similarity	NPD6881	Approved
0.8224	Intermediate Similarity	NPD7320	Approved
0.8148	Intermediate Similarity	NPD6372	Approved
0.8148	Intermediate Similarity	NPD6373	Approved
0.8131	Intermediate Similarity	NPD5697	Approved
0.8131	Intermediate Similarity	NPD6412	Phase 2
0.8131	Intermediate Similarity	NPD5701	Approved
0.8125	Intermediate Similarity	NPD4786	Approved
0.8095	Intermediate Similarity	NPD5226	Approved
0.8095	Intermediate Similarity	NPD5225	Approved
0.8095	Intermediate Similarity	NPD5224	Approved
0.8095	Intermediate Similarity	NPD4633	Approved
0.8081	Intermediate Similarity	NPD5328	Approved
0.8073	Intermediate Similarity	NPD7290	Approved
0.8073	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD6883	Approved
0.802	Intermediate Similarity	NPD6399	Phase 3
0.802	Intermediate Similarity	NPD4202	Approved
0.8019	Intermediate Similarity	NPD5174	Approved
0.8019	Intermediate Similarity	NPD5175	Approved
0.8	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6649	Approved
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6013	Approved
0.7982	Intermediate Similarity	NPD6014	Approved
0.7982	Intermediate Similarity	NPD6012	Approved
0.7965	Intermediate Similarity	NPD7115	Discovery
0.7928	Intermediate Similarity	NPD6882	Approved
0.7921	Intermediate Similarity	NPD6079	Approved
0.7917	Intermediate Similarity	NPD3667	Approved
0.7909	Intermediate Similarity	NPD4634	Approved
0.79	Intermediate Similarity	NPD4753	Phase 2
0.789	Intermediate Similarity	NPD6011	Approved
0.7885	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD6083	Phase 2
0.787	Intermediate Similarity	NPD4767	Approved
0.787	Intermediate Similarity	NPD4768	Approved
0.7857	Intermediate Similarity	NPD4632	Approved
0.785	Intermediate Similarity	NPD4754	Approved
0.7838	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6059	Approved
0.7759	Intermediate Similarity	NPD6319	Approved
0.7759	Intermediate Similarity	NPD6054	Approved
0.7755	Intermediate Similarity	NPD3665	Phase 1
0.7755	Intermediate Similarity	NPD3666	Approved
0.7755	Intermediate Similarity	NPD3133	Approved
0.7731	Intermediate Similarity	NPD7507	Approved
0.7727	Intermediate Similarity	NPD4729	Approved
0.7727	Intermediate Similarity	NPD5128	Approved
0.7727	Intermediate Similarity	NPD4730	Approved
0.7627	Intermediate Similarity	NPD6370	Approved
0.7619	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5221	Approved
0.7619	Intermediate Similarity	NPD5222	Approved
0.7619	Intermediate Similarity	NPD4697	Phase 3
0.76	Intermediate Similarity	NPD3618	Phase 1
0.7589	Intermediate Similarity	NPD5249	Phase 3
0.7589	Intermediate Similarity	NPD5247	Approved
0.7589	Intermediate Similarity	NPD5248	Approved
0.7589	Intermediate Similarity	NPD5251	Approved
0.7589	Intermediate Similarity	NPD5250	Approved
0.7565	Intermediate Similarity	NPD6274	Approved
0.7551	Intermediate Similarity	NPD4223	Phase 3
0.7551	Intermediate Similarity	NPD4221	Approved
0.7547	Intermediate Similarity	NPD5173	Approved
0.7545	Intermediate Similarity	NPD6008	Approved
0.7542	Intermediate Similarity	NPD6016	Approved
0.7542	Intermediate Similarity	NPD6015	Approved
0.7541	Intermediate Similarity	NPD7319	Approved
0.7524	Intermediate Similarity	NPD5695	Phase 3
0.7524	Intermediate Similarity	NPD5210	Approved
0.7524	Intermediate Similarity	NPD4629	Approved
0.7522	Intermediate Similarity	NPD5216	Approved
0.7522	Intermediate Similarity	NPD5217	Approved
0.7522	Intermediate Similarity	NPD5215	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7479	Intermediate Similarity	NPD5988	Approved
0.7477	Intermediate Similarity	NPD5696	Approved
0.7459	Intermediate Similarity	NPD7736	Approved
0.7451	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD6335	Approved
0.7434	Intermediate Similarity	NPD5135	Approved
0.7434	Intermediate Similarity	NPD5169	Approved
0.7434	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6409	Approved
0.7426	Intermediate Similarity	NPD6684	Approved
0.7426	Intermediate Similarity	NPD5330	Approved
0.7426	Intermediate Similarity	NPD7334	Approved
0.7426	Intermediate Similarity	NPD7146	Approved
0.7426	Intermediate Similarity	NPD7521	Approved
0.7417	Intermediate Similarity	NPD7604	Phase 2
0.74	Intermediate Similarity	NPD4197	Approved
0.74	Intermediate Similarity	NPD3668	Phase 3
0.7395	Intermediate Similarity	NPD6909	Approved
0.7395	Intermediate Similarity	NPD6908	Approved
0.7395	Intermediate Similarity	NPD5983	Phase 2
0.7377	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD8293	Discontinued
0.7368	Intermediate Similarity	NPD5127	Approved
0.7353	Intermediate Similarity	NPD7524	Approved
0.735	Intermediate Similarity	NPD6317	Approved
0.7347	Intermediate Similarity	NPD7525	Registered
0.73	Intermediate Similarity	NPD4788	Approved
0.7295	Intermediate Similarity	NPD6336	Discontinued
0.7292	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6314	Approved
0.7288	Intermediate Similarity	NPD6313	Approved
0.7282	Intermediate Similarity	NPD6903	Approved
0.7264	Intermediate Similarity	NPD7748	Approved
0.7255	Intermediate Similarity	NPD4688	Approved
0.7255	Intermediate Similarity	NPD4689	Approved
0.7255	Intermediate Similarity	NPD4138	Approved
0.7255	Intermediate Similarity	NPD5205	Approved
0.7255	Intermediate Similarity	NPD4693	Phase 3
0.7255	Intermediate Similarity	NPD6098	Approved
0.7255	Intermediate Similarity	NPD4690	Approved
0.7248	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD7639	Approved
0.7238	Intermediate Similarity	NPD7515	Phase 2
0.7238	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7902	Approved
0.7212	Intermediate Similarity	NPD6080	Approved
0.7212	Intermediate Similarity	NPD6673	Approved
0.7212	Intermediate Similarity	NPD6904	Approved
0.7196	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7339	Approved
0.7184	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5167	Approved
0.7177	Intermediate Similarity	NPD6033	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7638	Approved
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD7327	Approved
0.7129	Intermediate Similarity	NPD6695	Phase 3
0.7115	Intermediate Similarity	NPD5737	Approved
0.7115	Intermediate Similarity	NPD6672	Approved
0.7107	Intermediate Similarity	NPD8033	Approved
0.7107	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8133	Approved
0.7087	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5690	Phase 2
0.7087	Intermediate Similarity	NPD5280	Approved
0.7087	Intermediate Similarity	NPD5279	Phase 3
0.7087	Intermediate Similarity	NPD4694	Approved
0.7083	Intermediate Similarity	NPD7516	Approved
0.7075	Intermediate Similarity	NPD6411	Approved
0.7075	Intermediate Similarity	NPD5284	Approved
0.7075	Intermediate Similarity	NPD5281	Approved
0.7075	Intermediate Similarity	NPD5693	Phase 1
0.7043	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6435	Approved
0.7025	Intermediate Similarity	NPD8294	Approved
0.7025	Intermediate Similarity	NPD8377	Approved
0.7019	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD8328	Phase 3
0.6975	Remote Similarity	NPD6868	Approved
0.6967	Remote Similarity	NPD8380	Approved
0.6967	Remote Similarity	NPD8379	Approved
0.6967	Remote Similarity	NPD8296	Approved
0.6967	Remote Similarity	NPD7503	Approved
0.6967	Remote Similarity	NPD8335	Approved
0.6967	Remote Similarity	NPD8378	Approved
0.6957	Remote Similarity	NPD5168	Approved
0.6957	Remote Similarity	NPD6686	Approved
0.6952	Remote Similarity	NPD5208	Approved
0.6944	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7900	Approved
0.6939	Remote Similarity	NPD6933	Approved
0.6931	Remote Similarity	NPD4692	Approved
0.6931	Remote Similarity	NPD4139	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6050	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