NPASS Compound

Structure

NPC83709 OpenBabel07101718182D 35 39 0 0 1 0 0 0 0 0999 V2000 5.1504 -2.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2549 -1.1294 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 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 4.3414 -1.5361 0.0000 C 0 0 0 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 3.7536 -2.3452 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 25 1 0 0 0 0 2 25 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 18 2 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 16 28 1 0 0 0 0 17 13 1 1 0 0 0 17 35 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 6 0 0 0 20 15 1 1 0 0 0 20 24 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 28 1 6 0 0 0 24 29 1 0 0 0 0 25 33 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:	488.35
Volume:	523.332
LogP:	4.343
LogD:	3.431
LogS:	-4.693
# 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:	0.486
Synthetic Accessibility Score:	5.419
Fsp3:	0.9
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:	-4.871
MDCK Permeability:	1.3198552551330067e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.173
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	67.15998077392578%
Volume Distribution (VD):	0.919
Pgp-substrate:	16.512617111206055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	10.326
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.261
Carcinogencity:	0.874
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC83709

Natural Product ID:	NPC83709
*Common Name:**	Elaeocarpucin F
IUPAC Name:	n.a.
Synonyms:	Elaeocarpucin F
Standard InCHIKey:	USZRIUNXJIEEBG-FWTJSEBVSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-25(2,33)13-17-14-29(7,34)24-20(35-17)15-27(5)21-11-9-18-19(10-12-22(31)26(18,3)4)30(21,8)23(32)16-28(24,27)6/h9,17,19-22,24,31,33-34H,10-16H2,1-8H3/t17-,19+,20+,21-,22-,24-,27-,28+,29-,30-/m0/s1
SMILES:	O=C1C[C@]2(C)[C@@H]3[C@@H](C[C@]2([C@H]2[C@]1(C)[C@@H]1CC[C@@H](C(C1=CC2)(C)C)O)C)O[C@H](C[C@]3(C)O)CC(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023381
PubChem CID:	57379941
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[523577]

☑ 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 NPC83709 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	203
0.1-0.2	1292
0.2-0.3	4797
0.3-0.4	11051
0.4-0.5	10633
0.5-0.6	5807
0.6-0.7	5198
0.7-0.8	3356
0.8-0.85	330
0.85-0.9	18
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC185530
0.9278	High Similarity	NPC26478
0.9184	High Similarity	NPC149124
0.9184	High Similarity	NPC75531
0.9184	High Similarity	NPC137657
0.9158	High Similarity	NPC190554
0.9091	High Similarity	NPC60681
0.9	High Similarity	NPC144459
0.8969	High Similarity	NPC15390
0.8911	High Similarity	NPC177064
0.89	High Similarity	NPC278628
0.89	High Similarity	NPC231530
0.8889	High Similarity	NPC191892
0.8866	High Similarity	NPC477854
0.8854	High Similarity	NPC49371
0.875	High Similarity	NPC469599
0.8725	High Similarity	NPC94529
0.866	High Similarity	NPC173272
0.866	High Similarity	NPC477853
0.8646	High Similarity	NPC111015
0.8627	High Similarity	NPC165873
0.8617	High Similarity	NPC76879
0.8617	High Similarity	NPC32830
0.8617	High Similarity	NPC31985
0.8617	High Similarity	NPC474245
0.8617	High Similarity	NPC1015
0.8617	High Similarity	NPC186688
0.86	High Similarity	NPC22388
0.8571	High Similarity	NPC18509
0.8571	High Similarity	NPC280782
0.8558	High Similarity	NPC197428
0.8557	High Similarity	NPC472485
0.8557	High Similarity	NPC48330
0.8542	High Similarity	NPC206810
0.8529	High Similarity	NPC149047
0.8529	High Similarity	NPC196528
0.8526	High Similarity	NPC171441
0.8515	High Similarity	NPC140723
0.8511	High Similarity	NPC53911
0.8511	High Similarity	NPC193360
0.8511	High Similarity	NPC328313
0.85	High Similarity	NPC474327
0.8491	Intermediate Similarity	NPC194100
0.8478	Intermediate Similarity	NPC221758
0.8478	Intermediate Similarity	NPC82902
0.8478	Intermediate Similarity	NPC59453
0.8469	Intermediate Similarity	NPC42042
0.8454	Intermediate Similarity	NPC245972
0.8454	Intermediate Similarity	NPC196485
0.8447	Intermediate Similarity	NPC220229
0.8447	Intermediate Similarity	NPC475060
0.8447	Intermediate Similarity	NPC83744
0.8447	Intermediate Similarity	NPC59530
0.8447	Intermediate Similarity	NPC477916
0.8431	Intermediate Similarity	NPC471293
0.8431	Intermediate Similarity	NPC204833
0.8431	Intermediate Similarity	NPC209502
0.8421	Intermediate Similarity	NPC477943
0.8416	Intermediate Similarity	NPC473928
0.8404	Intermediate Similarity	NPC90652
0.8404	Intermediate Similarity	NPC475740
0.8404	Intermediate Similarity	NPC317590
0.84	Intermediate Similarity	NPC218383
0.84	Intermediate Similarity	NPC154072
0.84	Intermediate Similarity	NPC110149
0.84	Intermediate Similarity	NPC144956
0.84	Intermediate Similarity	NPC474720
0.8396	Intermediate Similarity	NPC207251
0.8387	Intermediate Similarity	NPC474218
0.8381	Intermediate Similarity	NPC154856
0.8381	Intermediate Similarity	NPC475317
0.8381	Intermediate Similarity	NPC76084
0.8381	Intermediate Similarity	NPC52241
0.837	Intermediate Similarity	NPC476082
0.837	Intermediate Similarity	NPC278648
0.8367	Intermediate Similarity	NPC473170
0.8367	Intermediate Similarity	NPC127063
0.8367	Intermediate Similarity	NPC472932
0.8367	Intermediate Similarity	NPC279974
0.8365	Intermediate Similarity	NPC329417
0.8365	Intermediate Similarity	NPC217201
0.835	Intermediate Similarity	NPC97202
0.835	Intermediate Similarity	NPC48733
0.835	Intermediate Similarity	NPC296945
0.835	Intermediate Similarity	NPC49958
0.835	Intermediate Similarity	NPC260268
0.835	Intermediate Similarity	NPC150531
0.835	Intermediate Similarity	NPC50692
0.835	Intermediate Similarity	NPC202167
0.835	Intermediate Similarity	NPC319077
0.835	Intermediate Similarity	NPC476027
0.835	Intermediate Similarity	NPC152695
0.835	Intermediate Similarity	NPC171137
0.835	Intermediate Similarity	NPC85829
0.835	Intermediate Similarity	NPC214264
0.835	Intermediate Similarity	NPC257353
0.835	Intermediate Similarity	NPC302607
0.8333	Intermediate Similarity	NPC117185
0.8333	Intermediate Similarity	NPC320026
0.8318	Intermediate Similarity	NPC178981
0.8318	Intermediate Similarity	NPC317210
0.8316	Intermediate Similarity	NPC470417
0.8316	Intermediate Similarity	NPC328539
0.8302	Intermediate Similarity	NPC43775
0.83	Intermediate Similarity	NPC119036
0.83	Intermediate Similarity	NPC114274
0.8298	Intermediate Similarity	NPC469994
0.8298	Intermediate Similarity	NPC145879
0.8298	Intermediate Similarity	NPC51014
0.8298	Intermediate Similarity	NPC20688
0.8298	Intermediate Similarity	NPC474778
0.8298	Intermediate Similarity	NPC31564
0.8298	Intermediate Similarity	NPC474732
0.8298	Intermediate Similarity	NPC474733
0.8286	Intermediate Similarity	NPC11710
0.8269	Intermediate Similarity	NPC44063
0.8269	Intermediate Similarity	NPC185
0.8269	Intermediate Similarity	NPC42847
0.8269	Intermediate Similarity	NPC64844
0.8265	Intermediate Similarity	NPC67831
0.8265	Intermediate Similarity	NPC174051
0.8261	Intermediate Similarity	NPC151519
0.8252	Intermediate Similarity	NPC29705
0.8247	Intermediate Similarity	NPC168027
0.8247	Intermediate Similarity	NPC131872
0.8247	Intermediate Similarity	NPC154101
0.8247	Intermediate Similarity	NPC262870
0.8247	Intermediate Similarity	NPC185936
0.8241	Intermediate Similarity	NPC326542
0.8235	Intermediate Similarity	NPC477054
0.8235	Intermediate Similarity	NPC87351
0.8235	Intermediate Similarity	NPC193934
0.8235	Intermediate Similarity	NPC477915
0.8235	Intermediate Similarity	NPC473424
0.8235	Intermediate Similarity	NPC271980
0.8229	Intermediate Similarity	NPC474704
0.8229	Intermediate Similarity	NPC326627
0.8229	Intermediate Similarity	NPC86319
0.8229	Intermediate Similarity	NPC310010
0.8229	Intermediate Similarity	NPC275740
0.8229	Intermediate Similarity	NPC2983
0.8229	Intermediate Similarity	NPC475921
0.8224	Intermediate Similarity	NPC130427
0.8224	Intermediate Similarity	NPC474265
0.8224	Intermediate Similarity	NPC71348
0.8224	Intermediate Similarity	NPC210420
0.8218	Intermediate Similarity	NPC167974
0.8211	Intermediate Similarity	NPC472481
0.8211	Intermediate Similarity	NPC472482
0.8211	Intermediate Similarity	NPC472484
0.8211	Intermediate Similarity	NPC58063
0.8208	Intermediate Similarity	NPC163314
0.82	Intermediate Similarity	NPC108078
0.8191	Intermediate Similarity	NPC469948
0.8191	Intermediate Similarity	NPC202868
0.819	Intermediate Similarity	NPC65941
0.8182	Intermediate Similarity	NPC317586
0.8182	Intermediate Similarity	NPC200702
0.8182	Intermediate Similarity	NPC470016
0.8182	Intermediate Similarity	NPC271195
0.8173	Intermediate Similarity	NPC210178
0.8173	Intermediate Similarity	NPC475571
0.8163	Intermediate Similarity	NPC472930
0.8163	Intermediate Similarity	NPC470375
0.8163	Intermediate Similarity	NPC477855
0.8163	Intermediate Similarity	NPC470376
0.8163	Intermediate Similarity	NPC472942
0.8155	Intermediate Similarity	NPC247957
0.8155	Intermediate Similarity	NPC311612
0.8155	Intermediate Similarity	NPC249187
0.8148	Intermediate Similarity	NPC52634
0.8148	Intermediate Similarity	NPC250109
0.8148	Intermediate Similarity	NPC260665
0.8148	Intermediate Similarity	NPC202889
0.8148	Intermediate Similarity	NPC108721
0.8148	Intermediate Similarity	NPC255017
0.8148	Intermediate Similarity	NPC962
0.8148	Intermediate Similarity	NPC73300
0.8144	Intermediate Similarity	NPC48010
0.8144	Intermediate Similarity	NPC20388
0.8144	Intermediate Similarity	NPC136801
0.8144	Intermediate Similarity	NPC471896
0.8137	Intermediate Similarity	NPC477051
0.8137	Intermediate Similarity	NPC477052
0.8137	Intermediate Similarity	NPC476897
0.8137	Intermediate Similarity	NPC477053
0.8131	Intermediate Similarity	NPC471243
0.8125	Intermediate Similarity	NPC471722
0.8125	Intermediate Similarity	NPC143767
0.8125	Intermediate Similarity	NPC131470
0.8125	Intermediate Similarity	NPC470921
0.8119	Intermediate Similarity	NPC58942
0.8119	Intermediate Similarity	NPC260149
0.8119	Intermediate Similarity	NPC191565
0.8119	Intermediate Similarity	NPC153792
0.8119	Intermediate Similarity	NPC271387
0.8113	Intermediate Similarity	NPC2766
0.8113	Intermediate Similarity	NPC214644
0.8113	Intermediate Similarity	NPC470615
0.8113	Intermediate Similarity	NPC241927

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 NPC83709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1541
0.2-0.3	4033
0.3-0.4	2274
0.4-0.5	627
0.5-0.6	166
0.6-0.7	146
0.7-0.8	143
0.8-0.85	51
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4755	Approved
0.8529	High Similarity	NPD5739	Approved
0.8529	High Similarity	NPD7128	Approved
0.8529	High Similarity	NPD6675	Approved
0.8529	High Similarity	NPD6402	Approved
0.8478	Intermediate Similarity	NPD4786	Approved
0.8421	Intermediate Similarity	NPD5328	Approved
0.84	Intermediate Similarity	NPD5286	Approved
0.84	Intermediate Similarity	NPD4696	Approved
0.84	Intermediate Similarity	NPD5285	Approved
0.84	Intermediate Similarity	NPD4700	Approved
0.8365	Intermediate Similarity	NPD6899	Approved
0.8365	Intermediate Similarity	NPD6881	Approved
0.8365	Intermediate Similarity	NPD7320	Approved
0.8286	Intermediate Similarity	NPD6372	Approved
0.8286	Intermediate Similarity	NPD6373	Approved
0.8269	Intermediate Similarity	NPD5701	Approved
0.8269	Intermediate Similarity	NPD5697	Approved
0.8261	Intermediate Similarity	NPD3667	Approved
0.8247	Intermediate Similarity	NPD6079	Approved
0.8235	Intermediate Similarity	NPD5225	Approved
0.8235	Intermediate Similarity	NPD5226	Approved
0.8235	Intermediate Similarity	NPD4633	Approved
0.8235	Intermediate Similarity	NPD5211	Phase 2
0.8235	Intermediate Similarity	NPD5224	Approved
0.8229	Intermediate Similarity	NPD4753	Phase 2
0.8208	Intermediate Similarity	NPD7290	Approved
0.8208	Intermediate Similarity	NPD7102	Approved
0.8208	Intermediate Similarity	NPD6883	Approved
0.82	Intermediate Similarity	NPD6084	Phase 2
0.82	Intermediate Similarity	NPD6083	Phase 2
0.8163	Intermediate Similarity	NPD6399	Phase 3
0.8163	Intermediate Similarity	NPD4202	Approved
0.8155	Intermediate Similarity	NPD5175	Approved
0.8155	Intermediate Similarity	NPD5174	Approved
0.8137	Intermediate Similarity	NPD5223	Approved
0.8131	Intermediate Similarity	NPD6869	Approved
0.8131	Intermediate Similarity	NPD8130	Phase 1
0.8131	Intermediate Similarity	NPD6649	Approved
0.8131	Intermediate Similarity	NPD6847	Approved
0.8131	Intermediate Similarity	NPD6617	Approved
0.8131	Intermediate Similarity	NPD6650	Approved
0.8113	Intermediate Similarity	NPD6013	Approved
0.8113	Intermediate Similarity	NPD6012	Approved
0.8113	Intermediate Similarity	NPD6014	Approved
0.8095	Intermediate Similarity	NPD6412	Phase 2
0.8085	Intermediate Similarity	NPD3666	Approved
0.8085	Intermediate Similarity	NPD3665	Phase 1
0.8085	Intermediate Similarity	NPD3133	Approved
0.8077	Intermediate Similarity	NPD5141	Approved
0.8056	Intermediate Similarity	NPD8297	Approved
0.8056	Intermediate Similarity	NPD6882	Approved
0.8037	Intermediate Similarity	NPD4634	Approved
0.8019	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD4768	Approved
0.8	Intermediate Similarity	NPD4767	Approved
0.8	Intermediate Similarity	NPD6008	Approved
0.7981	Intermediate Similarity	NPD4754	Approved
0.7963	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD4697	Phase 3
0.7921	Intermediate Similarity	NPD5221	Approved
0.7921	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5222	Approved
0.7917	Intermediate Similarity	NPD3618	Phase 1
0.7876	Intermediate Similarity	NPD6059	Approved
0.7876	Intermediate Similarity	NPD6054	Approved
0.7872	Intermediate Similarity	NPD4221	Approved
0.7872	Intermediate Similarity	NPD4223	Phase 3
0.785	Intermediate Similarity	NPD5128	Approved
0.785	Intermediate Similarity	NPD4730	Approved
0.785	Intermediate Similarity	NPD4729	Approved
0.7843	Intermediate Similarity	NPD5173	Approved
0.7822	Intermediate Similarity	NPD5695	Phase 3
0.7822	Intermediate Similarity	NPD5210	Approved
0.7822	Intermediate Similarity	NPD4629	Approved
0.7818	Intermediate Similarity	NPD4632	Approved
0.7812	Intermediate Similarity	NPD5329	Approved
0.7767	Intermediate Similarity	NPD5696	Approved
0.7755	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6370	Approved
0.7732	Intermediate Similarity	NPD6409	Approved
0.7732	Intermediate Similarity	NPD6684	Approved
0.7732	Intermediate Similarity	NPD5330	Approved
0.7732	Intermediate Similarity	NPD7521	Approved
0.7732	Intermediate Similarity	NPD7334	Approved
0.7732	Intermediate Similarity	NPD7146	Approved
0.7719	Intermediate Similarity	NPD6319	Approved
0.7708	Intermediate Similarity	NPD3668	Phase 3
0.7708	Intermediate Similarity	NPD4197	Approved
0.7706	Intermediate Similarity	NPD5251	Approved
0.7706	Intermediate Similarity	NPD5250	Approved
0.7706	Intermediate Similarity	NPD5249	Phase 3
0.7706	Intermediate Similarity	NPD5247	Approved
0.7706	Intermediate Similarity	NPD5248	Approved
0.7679	Intermediate Similarity	NPD6274	Approved
0.7652	Intermediate Similarity	NPD6016	Approved
0.7652	Intermediate Similarity	NPD6015	Approved
0.7636	Intermediate Similarity	NPD5217	Approved
0.7636	Intermediate Similarity	NPD5215	Approved
0.7636	Intermediate Similarity	NPD5216	Approved
0.7632	Intermediate Similarity	NPD7101	Approved
0.7632	Intermediate Similarity	NPD7100	Approved
0.7611	Intermediate Similarity	NPD6009	Approved
0.7609	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7492	Approved
0.7604	Intermediate Similarity	NPD4788	Approved
0.7596	Intermediate Similarity	NPD7638	Approved
0.7586	Intermediate Similarity	NPD5988	Approved
0.7576	Intermediate Similarity	NPD6903	Approved
0.7563	Intermediate Similarity	NPD7736	Approved
0.7551	Intermediate Similarity	NPD4688	Approved
0.7551	Intermediate Similarity	NPD4138	Approved
0.7551	Intermediate Similarity	NPD4689	Approved
0.7551	Intermediate Similarity	NPD6098	Approved
0.7551	Intermediate Similarity	NPD4690	Approved
0.7551	Intermediate Similarity	NPD4693	Phase 3
0.7551	Intermediate Similarity	NPD5205	Approved
0.7549	Intermediate Similarity	NPD7748	Approved
0.7545	Intermediate Similarity	NPD5169	Approved
0.7545	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5135	Approved
0.7544	Intermediate Similarity	NPD6335	Approved
0.7542	Intermediate Similarity	NPD7507	Approved
0.7542	Intermediate Similarity	NPD6616	Approved
0.7525	Intermediate Similarity	NPD7515	Phase 2
0.7524	Intermediate Similarity	NPD7640	Approved
0.7524	Intermediate Similarity	NPD7639	Approved
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6909	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD6908	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.7479	Intermediate Similarity	NPD7078	Approved
0.7479	Intermediate Similarity	NPD8293	Discontinued
0.7477	Intermediate Similarity	NPD5127	Approved
0.7476	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7525	Registered
0.7456	Intermediate Similarity	NPD7115	Discovery
0.7456	Intermediate Similarity	NPD6317	Approved
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6695	Phase 3
0.7411	Intermediate Similarity	NPD6053	Discontinued
0.74	Intermediate Similarity	NPD6672	Approved
0.74	Intermediate Similarity	NPD5737	Approved
0.7395	Intermediate Similarity	NPD6336	Discontinued
0.7391	Intermediate Similarity	NPD6313	Approved
0.7391	Intermediate Similarity	NPD6314	Approved
0.7374	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5280	Approved
0.7374	Intermediate Similarity	NPD5279	Phase 3
0.7374	Intermediate Similarity	NPD4694	Approved
0.7374	Intermediate Similarity	NPD5690	Phase 2
0.7355	Intermediate Similarity	NPD7319	Approved
0.7353	Intermediate Similarity	NPD8035	Phase 2
0.7353	Intermediate Similarity	NPD6411	Approved
0.7353	Intermediate Similarity	NPD8034	Phase 2
0.7347	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7902	Approved
0.73	Intermediate Similarity	NPD3573	Approved
0.7281	Intermediate Similarity	NPD5167	Approved
0.7273	Intermediate Similarity	NPD6033	Approved
0.7228	Intermediate Similarity	NPD5208	Approved
0.7217	Intermediate Similarity	NPD6868	Approved
0.7216	Intermediate Similarity	NPD4139	Approved
0.7216	Intermediate Similarity	NPD4692	Approved
0.7207	Intermediate Similarity	NPD5168	Approved
0.7204	Intermediate Similarity	NPD4784	Approved
0.7204	Intermediate Similarity	NPD4785	Approved
0.7203	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4195	Approved
0.7188	Intermediate Similarity	NPD7645	Phase 2
0.7184	Intermediate Similarity	NPD5693	Phase 1
0.7184	Intermediate Similarity	NPD5284	Approved
0.7184	Intermediate Similarity	NPD5281	Approved
0.7184	Intermediate Similarity	NPD6050	Approved
0.7174	Intermediate Similarity	NPD4243	Approved
0.7157	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD6435	Approved
0.7129	Intermediate Similarity	NPD7524	Approved
0.7129	Intermediate Similarity	NPD7750	Discontinued
0.7128	Intermediate Similarity	NPD3703	Phase 2
0.7113	Intermediate Similarity	NPD6931	Approved
0.7113	Intermediate Similarity	NPD6930	Phase 2
0.7087	Intermediate Similarity	NPD5692	Phase 3
0.7048	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6001	Approved
0.7048	Intermediate Similarity	NPD7900	Approved
0.7021	Intermediate Similarity	NPD6924	Approved
0.7021	Intermediate Similarity	NPD6926	Approved
0.7019	Intermediate Similarity	NPD7637	Suspended
0.7019	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD6929	Approved
0.6991	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6051	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