NPASS Compound

Structure

NPC177064 OpenBabel07101718282D 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 2 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:	484.32
Volume:	518.059
LogP:	4.354
LogD:	3.461
LogS:	-4.819
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	5.539
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.011
MDCK Permeability:	1.250984405487543e-05
Pgp-inhibitor:	0.832
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.637
30% Bioavailability (F30%):	0.156

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	75.9007339477539%
Volume Distribution (VD):	2.157
Pgp-substrate:	13.209797859191895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.42
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.186
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	8.376
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.33
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.541
Carcinogencity:	0.88
Eye Corrosion:	0.017
Eye Irritation:	0.019
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC177064

Natural Product ID:	NPC177064
*Common Name:**	Elaeocarpucin E
IUPAC Name:	n.a.
Synonyms:	Elaeocarpucin E
Standard InCHIKey:	NZGITYVJSRBFQS-HHMFILIPSA-N
Standard InCHI:	InChI=1S/C30H44O5/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/h8,12,16,18,20-23,25,32,34H,9-11,13-15H2,1-7H3/b17-12+/t18-,20+,21+,22-,23-,25-,27-,28+,29-,30-/m0/s1
SMILES:	C/C(=C[C@H]1C[C@@](C)([C@H]2[C@@H](C[C@@]3(C)[C@@H]4CC=C5[C@@H](CC[C@@H](C5(C)C)O)[C@]4(C)C(=O)C[C@]23C)O1)O)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023380
PubChem CID:	57379940
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	1

Activity Type	# Activity
Cell Line	1

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[468983]

☑ 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 NPC177064 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	214
0.1-0.2	1337
0.2-0.3	4295
0.3-0.4	9126
0.4-0.5	12276
0.5-0.6	6456
0.6-0.7	6156
0.7-0.8	2645
0.8-0.85	178
0.85-0.9	9
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC60681
0.9495	High Similarity	NPC185530
0.94	High Similarity	NPC26478
0.9126	High Similarity	NPC144459
0.8932	High Similarity	NPC137657
0.8911	High Similarity	NPC83709
0.875	High Similarity	NPC149124
0.875	High Similarity	NPC75531
0.8585	High Similarity	NPC185
0.8558	High Similarity	NPC87351
0.8558	High Similarity	NPC473424
0.8532	High Similarity	NPC475524
0.8532	High Similarity	NPC100267
0.8529	High Similarity	NPC291634
0.8529	High Similarity	NPC126815
0.8515	High Similarity	NPC472932
0.8482	Intermediate Similarity	NPC257457
0.8482	Intermediate Similarity	NPC311554
0.8476	Intermediate Similarity	NPC311612
0.8462	Intermediate Similarity	NPC474327
0.8462	Intermediate Similarity	NPC310981
0.8455	Intermediate Similarity	NPC73050
0.8426	Intermediate Similarity	NPC214644
0.8411	Intermediate Similarity	NPC475294
0.84	Intermediate Similarity	NPC472975
0.8393	Intermediate Similarity	NPC476965
0.8393	Intermediate Similarity	NPC470959
0.8384	Intermediate Similarity	NPC31985
0.8384	Intermediate Similarity	NPC1015
0.8381	Intermediate Similarity	NPC477915
0.8378	Intermediate Similarity	NPC238667
0.8365	Intermediate Similarity	NPC144956
0.8364	Intermediate Similarity	NPC221144
0.835	Intermediate Similarity	NPC18509
0.8319	Intermediate Similarity	NPC329736
0.8318	Intermediate Similarity	NPC478052
0.8318	Intermediate Similarity	NPC149047
0.8317	Intermediate Similarity	NPC472930
0.8304	Intermediate Similarity	NPC469794
0.8304	Intermediate Similarity	NPC148458
0.8304	Intermediate Similarity	NPC72772
0.8302	Intermediate Similarity	NPC111323
0.8302	Intermediate Similarity	NPC112009
0.83	Intermediate Similarity	NPC48010
0.8288	Intermediate Similarity	NPC122056
0.8276	Intermediate Similarity	NPC204812
0.8276	Intermediate Similarity	NPC473979
0.8269	Intermediate Similarity	NPC197386
0.8252	Intermediate Similarity	NPC249954
0.8252	Intermediate Similarity	NPC78473
0.8252	Intermediate Similarity	NPC471463
0.8246	Intermediate Similarity	NPC475041
0.8246	Intermediate Similarity	NPC264954
0.8246	Intermediate Similarity	NPC476960
0.8246	Intermediate Similarity	NPC473270
0.8246	Intermediate Similarity	NPC61520
0.8241	Intermediate Similarity	NPC44063
0.8241	Intermediate Similarity	NPC220229
0.8241	Intermediate Similarity	NPC477916
0.8241	Intermediate Similarity	NPC475060
0.8241	Intermediate Similarity	NPC83744
0.8235	Intermediate Similarity	NPC292793
0.823	Intermediate Similarity	NPC239273
0.823	Intermediate Similarity	NPC474518
0.823	Intermediate Similarity	NPC471854
0.8224	Intermediate Similarity	NPC204833
0.8224	Intermediate Similarity	NPC209502
0.8224	Intermediate Similarity	NPC472868
0.8218	Intermediate Similarity	NPC472978
0.8214	Intermediate Similarity	NPC470953
0.8214	Intermediate Similarity	NPC147912
0.8214	Intermediate Similarity	NPC67259
0.8208	Intermediate Similarity	NPC136289
0.8205	Intermediate Similarity	NPC241456
0.8205	Intermediate Similarity	NPC32868
0.82	Intermediate Similarity	NPC477943
0.8198	Intermediate Similarity	NPC476163
0.8198	Intermediate Similarity	NPC191620
0.8198	Intermediate Similarity	NPC207251
0.819	Intermediate Similarity	NPC154072
0.8182	Intermediate Similarity	NPC475740
0.8182	Intermediate Similarity	NPC37116
0.8182	Intermediate Similarity	NPC197428
0.8182	Intermediate Similarity	NPC76084
0.8174	Intermediate Similarity	NPC184555
0.8174	Intermediate Similarity	NPC79579
0.8174	Intermediate Similarity	NPC476962
0.8174	Intermediate Similarity	NPC474370
0.8174	Intermediate Similarity	NPC476961
0.8173	Intermediate Similarity	NPC151488
0.8173	Intermediate Similarity	NPC190554
0.8173	Intermediate Similarity	NPC253826
0.8165	Intermediate Similarity	NPC65941
0.8165	Intermediate Similarity	NPC472825
0.8165	Intermediate Similarity	NPC217201
0.8165	Intermediate Similarity	NPC329417
0.8158	Intermediate Similarity	NPC153440
0.8155	Intermediate Similarity	NPC259286
0.8155	Intermediate Similarity	NPC469599
0.8155	Intermediate Similarity	NPC473170
0.8148	Intermediate Similarity	NPC171137
0.8148	Intermediate Similarity	NPC152695
0.8148	Intermediate Similarity	NPC202167
0.8148	Intermediate Similarity	NPC296945
0.8148	Intermediate Similarity	NPC85829
0.8148	Intermediate Similarity	NPC319077
0.8148	Intermediate Similarity	NPC302607
0.8148	Intermediate Similarity	NPC97202
0.8148	Intermediate Similarity	NPC257353
0.8148	Intermediate Similarity	NPC260268
0.8148	Intermediate Similarity	NPC49958
0.8148	Intermediate Similarity	NPC214264
0.8148	Intermediate Similarity	NPC150531
0.8148	Intermediate Similarity	NPC50692
0.8148	Intermediate Similarity	NPC476027
0.8148	Intermediate Similarity	NPC48733
0.8142	Intermediate Similarity	NPC196931
0.8142	Intermediate Similarity	NPC190286
0.8142	Intermediate Similarity	NPC270929
0.8137	Intermediate Similarity	NPC250575
0.8137	Intermediate Similarity	NPC69454
0.8131	Intermediate Similarity	NPC236390
0.8131	Intermediate Similarity	NPC180204
0.8125	Intermediate Similarity	NPC317210
0.812	Intermediate Similarity	NPC55602
0.8119	Intermediate Similarity	NPC191684
0.8119	Intermediate Similarity	NPC183283
0.8119	Intermediate Similarity	NPC320026
0.8113	Intermediate Similarity	NPC473174
0.8113	Intermediate Similarity	NPC81530
0.8113	Intermediate Similarity	NPC472637
0.8108	Intermediate Similarity	NPC470960
0.8108	Intermediate Similarity	NPC43775
0.8108	Intermediate Similarity	NPC474315
0.8103	Intermediate Similarity	NPC46570
0.8103	Intermediate Similarity	NPC470878
0.8103	Intermediate Similarity	NPC473256
0.81	Intermediate Similarity	NPC328539
0.8095	Intermediate Similarity	NPC471784
0.8095	Intermediate Similarity	NPC176845
0.8095	Intermediate Similarity	NPC222011
0.8095	Intermediate Similarity	NPC303777
0.8091	Intermediate Similarity	NPC11710
0.8091	Intermediate Similarity	NPC41405
0.8091	Intermediate Similarity	NPC2766
0.8087	Intermediate Similarity	NPC5292
0.8081	Intermediate Similarity	NPC31564
0.8081	Intermediate Similarity	NPC474732
0.8081	Intermediate Similarity	NPC474778
0.8081	Intermediate Similarity	NPC474733
0.8081	Intermediate Similarity	NPC145879
0.8077	Intermediate Similarity	NPC160056
0.8077	Intermediate Similarity	NPC328371
0.8077	Intermediate Similarity	NPC192428
0.8073	Intermediate Similarity	NPC91034
0.807	Intermediate Similarity	NPC20302
0.807	Intermediate Similarity	NPC167606
0.807	Intermediate Similarity	NPC470492
0.807	Intermediate Similarity	NPC286528
0.807	Intermediate Similarity	NPC140055
0.807	Intermediate Similarity	NPC476959
0.8067	Intermediate Similarity	NPC287423
0.8058	Intermediate Similarity	NPC472976
0.8058	Intermediate Similarity	NPC8993
0.8058	Intermediate Similarity	NPC111015
0.8058	Intermediate Similarity	NPC472977
0.8056	Intermediate Similarity	NPC235889
0.8053	Intermediate Similarity	NPC326542
0.8039	Intermediate Similarity	NPC473998
0.8039	Intermediate Similarity	NPC475806
0.8039	Intermediate Similarity	NPC168027
0.8039	Intermediate Similarity	NPC272746
0.8039	Intermediate Similarity	NPC63748
0.8039	Intermediate Similarity	NPC185936
0.8037	Intermediate Similarity	NPC22388
0.8037	Intermediate Similarity	NPC155332
0.8037	Intermediate Similarity	NPC195290
0.8037	Intermediate Similarity	NPC32577
0.8037	Intermediate Similarity	NPC114540
0.8037	Intermediate Similarity	NPC204450
0.8036	Intermediate Similarity	NPC69291
0.8034	Intermediate Similarity	NPC107493
0.8034	Intermediate Similarity	NPC88326
0.8034	Intermediate Similarity	NPC269642
0.8034	Intermediate Similarity	NPC153700
0.802	Intermediate Similarity	NPC309603
0.802	Intermediate Similarity	NPC86319
0.802	Intermediate Similarity	NPC186688
0.802	Intermediate Similarity	NPC326627
0.802	Intermediate Similarity	NPC76879
0.802	Intermediate Similarity	NPC472973
0.802	Intermediate Similarity	NPC310010
0.802	Intermediate Similarity	NPC275740
0.802	Intermediate Similarity	NPC474245
0.802	Intermediate Similarity	NPC2983
0.802	Intermediate Similarity	NPC32830
0.802	Intermediate Similarity	NPC473999
0.8019	Intermediate Similarity	NPC201406
0.8019	Intermediate Similarity	NPC15390
0.8019	Intermediate Similarity	NPC474720

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 NPC177064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1542
0.2-0.3	3817
0.3-0.4	2403
0.4-0.5	712
0.5-0.6	166
0.6-0.7	160
0.7-0.8	130
0.8-0.85	37
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8381	Intermediate Similarity	NPD5211	Phase 2
0.8365	Intermediate Similarity	NPD4696	Approved
0.8365	Intermediate Similarity	NPD5286	Approved
0.8365	Intermediate Similarity	NPD5285	Approved
0.835	Intermediate Similarity	NPD4755	Approved
0.8333	Intermediate Similarity	NPD6881	Approved
0.8333	Intermediate Similarity	NPD6899	Approved
0.8318	Intermediate Similarity	NPD6675	Approved
0.8318	Intermediate Similarity	NPD5739	Approved
0.8318	Intermediate Similarity	NPD7128	Approved
0.8318	Intermediate Similarity	NPD6402	Approved
0.8241	Intermediate Similarity	NPD5697	Approved
0.8224	Intermediate Similarity	NPD5141	Approved
0.8218	Intermediate Similarity	NPD6079	Approved
0.8208	Intermediate Similarity	NPD5226	Approved
0.8208	Intermediate Similarity	NPD4633	Approved
0.8208	Intermediate Similarity	NPD5225	Approved
0.8208	Intermediate Similarity	NPD5224	Approved
0.82	Intermediate Similarity	NPD5328	Approved
0.819	Intermediate Similarity	NPD4700	Approved
0.8182	Intermediate Similarity	NPD7102	Approved
0.8182	Intermediate Similarity	NPD6883	Approved
0.8182	Intermediate Similarity	NPD7290	Approved
0.8165	Intermediate Similarity	NPD7320	Approved
0.8131	Intermediate Similarity	NPD5175	Approved
0.8131	Intermediate Similarity	NPD5174	Approved
0.8113	Intermediate Similarity	NPD5223	Approved
0.8108	Intermediate Similarity	NPD6869	Approved
0.8108	Intermediate Similarity	NPD6649	Approved
0.8108	Intermediate Similarity	NPD6847	Approved
0.8108	Intermediate Similarity	NPD8130	Phase 1
0.8108	Intermediate Similarity	NPD6650	Approved
0.8108	Intermediate Similarity	NPD6617	Approved
0.8091	Intermediate Similarity	NPD6014	Approved
0.8091	Intermediate Similarity	NPD6013	Approved
0.8091	Intermediate Similarity	NPD6372	Approved
0.8091	Intermediate Similarity	NPD6012	Approved
0.8091	Intermediate Similarity	NPD6373	Approved
0.8077	Intermediate Similarity	NPD4697	Phase 3
0.8073	Intermediate Similarity	NPD5701	Approved
0.807	Intermediate Similarity	NPD7115	Discovery
0.8036	Intermediate Similarity	NPD6882	Approved
0.8036	Intermediate Similarity	NPD8297	Approved
0.802	Intermediate Similarity	NPD4753	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6083	Phase 2
0.7983	Intermediate Similarity	NPD7507	Approved
0.7961	Intermediate Similarity	NPD4202	Approved
0.7905	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5222	Approved
0.7905	Intermediate Similarity	NPD5221	Approved
0.7879	Intermediate Similarity	NPD3666	Approved
0.7879	Intermediate Similarity	NPD4786	Approved
0.7879	Intermediate Similarity	NPD3133	Approved
0.7879	Intermediate Similarity	NPD3665	Phase 1
0.7838	Intermediate Similarity	NPD5128	Approved
0.7838	Intermediate Similarity	NPD4729	Approved
0.7838	Intermediate Similarity	NPD4730	Approved
0.783	Intermediate Similarity	NPD5173	Approved
0.7818	Intermediate Similarity	NPD4767	Approved
0.7818	Intermediate Similarity	NPD4768	Approved
0.781	Intermediate Similarity	NPD4629	Approved
0.781	Intermediate Similarity	NPD5210	Approved
0.7798	Intermediate Similarity	NPD4754	Approved
0.7788	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7319	Approved
0.7757	Intermediate Similarity	NPD7638	Approved
0.7723	Intermediate Similarity	NPD3618	Phase 1
0.7699	Intermediate Similarity	NPD5248	Approved
0.7699	Intermediate Similarity	NPD5249	Phase 3
0.7699	Intermediate Similarity	NPD5247	Approved
0.7699	Intermediate Similarity	NPD5250	Approved
0.7699	Intermediate Similarity	NPD4634	Approved
0.7699	Intermediate Similarity	NPD5251	Approved
0.7685	Intermediate Similarity	NPD7640	Approved
0.7685	Intermediate Similarity	NPD7639	Approved
0.7677	Intermediate Similarity	NPD4223	Phase 3
0.7677	Intermediate Similarity	NPD3667	Approved
0.7677	Intermediate Similarity	NPD4221	Approved
0.7672	Intermediate Similarity	NPD6274	Approved
0.7642	Intermediate Similarity	NPD5695	Phase 3
0.7632	Intermediate Similarity	NPD5217	Approved
0.7632	Intermediate Similarity	NPD5215	Approved
0.7632	Intermediate Similarity	NPD5216	Approved
0.7627	Intermediate Similarity	NPD7100	Approved
0.7627	Intermediate Similarity	NPD7101	Approved
0.7624	Intermediate Similarity	NPD5329	Approved
0.7619	Intermediate Similarity	NPD6399	Phase 3
0.7593	Intermediate Similarity	NPD5696	Approved
0.7589	Intermediate Similarity	NPD6412	Phase 2
0.7573	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD6053	Discontinued
0.7563	Intermediate Similarity	NPD6054	Approved
0.7549	Intermediate Similarity	NPD7521	Approved
0.7549	Intermediate Similarity	NPD7334	Approved
0.7549	Intermediate Similarity	NPD5330	Approved
0.7549	Intermediate Similarity	NPD6684	Approved
0.7549	Intermediate Similarity	NPD6409	Approved
0.7549	Intermediate Similarity	NPD7146	Approved
0.7544	Intermediate Similarity	NPD5169	Approved
0.7544	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5135	Approved
0.7542	Intermediate Similarity	NPD6335	Approved
0.7525	Intermediate Similarity	NPD4197	Approved
0.7524	Intermediate Similarity	NPD5693	Phase 1
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6008	Approved
0.7478	Intermediate Similarity	NPD5127	Approved
0.7458	Intermediate Similarity	NPD6317	Approved
0.7438	Intermediate Similarity	NPD6370	Approved
0.7426	Intermediate Similarity	NPD4788	Approved
0.7417	Intermediate Similarity	NPD6319	Approved
0.7417	Intermediate Similarity	NPD6059	Approved
0.7404	Intermediate Similarity	NPD6903	Approved
0.7395	Intermediate Similarity	NPD6314	Approved
0.7395	Intermediate Similarity	NPD6313	Approved
0.7383	Intermediate Similarity	NPD7748	Approved
0.7379	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5205	Approved
0.7379	Intermediate Similarity	NPD4690	Approved
0.7379	Intermediate Similarity	NPD4693	Phase 3
0.7379	Intermediate Similarity	NPD4138	Approved
0.7379	Intermediate Similarity	NPD4688	Approved
0.7379	Intermediate Similarity	NPD5690	Phase 2
0.7379	Intermediate Similarity	NPD4689	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7355	Intermediate Similarity	NPD6016	Approved
0.7355	Intermediate Similarity	NPD6015	Approved
0.7355	Intermediate Similarity	NPD6908	Approved
0.7355	Intermediate Similarity	NPD6909	Approved
0.7333	Intermediate Similarity	NPD6673	Approved
0.7333	Intermediate Similarity	NPD6904	Approved
0.7333	Intermediate Similarity	NPD6080	Approved
0.7317	Intermediate Similarity	NPD7492	Approved
0.7315	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6009	Approved
0.7308	Intermediate Similarity	NPD3573	Approved
0.7295	Intermediate Similarity	NPD5988	Approved
0.7288	Intermediate Similarity	NPD5167	Approved
0.728	Intermediate Similarity	NPD7736	Approved
0.7258	Intermediate Similarity	NPD6616	Approved
0.7238	Intermediate Similarity	NPD5737	Approved
0.7238	Intermediate Similarity	NPD6672	Approved
0.7236	Intermediate Similarity	NPD7604	Phase 2
0.7227	Intermediate Similarity	NPD6868	Approved
0.7217	Intermediate Similarity	NPD5168	Approved
0.7213	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5983	Phase 2
0.7212	Intermediate Similarity	NPD5279	Phase 3
0.7212	Intermediate Similarity	NPD4694	Approved
0.7212	Intermediate Similarity	NPD5280	Approved
0.72	Intermediate Similarity	NPD4195	Approved
0.72	Intermediate Similarity	NPD7078	Approved
0.7184	Intermediate Similarity	NPD3668	Phase 3
0.7182	Intermediate Similarity	NPD7902	Approved
0.717	Intermediate Similarity	NPD6051	Approved
0.712	Intermediate Similarity	NPD6336	Discontinued
0.7117	Intermediate Similarity	NPD4225	Approved
0.7107	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD7328	Approved
0.7103	Intermediate Similarity	NPD5785	Approved
0.708	Intermediate Similarity	NPD7632	Discontinued
0.7075	Intermediate Similarity	NPD5208	Approved
0.7073	Intermediate Similarity	NPD7503	Approved
0.7073	Intermediate Similarity	NPD8033	Approved
0.7071	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6686	Approved
0.7063	Intermediate Similarity	NPD8293	Discontinued
0.7049	Intermediate Similarity	NPD7516	Approved
0.7048	Intermediate Similarity	NPD6098	Approved
0.7037	Intermediate Similarity	NPD6050	Approved
0.7037	Intermediate Similarity	NPD5281	Approved
0.7037	Intermediate Similarity	NPD5284	Approved
0.6992	Remote Similarity	NPD8377	Approved
0.6992	Remote Similarity	NPD8294	Approved
0.699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6942	Approved
0.697	Remote Similarity	NPD7339	Approved
0.6961	Remote Similarity	NPD4695	Discontinued
0.6961	Remote Similarity	NPD7525	Registered
0.6952	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5692	Phase 3
0.6935	Remote Similarity	NPD8296	Approved
0.6935	Remote Similarity	NPD8378	Approved
0.6935	Remote Similarity	NPD8379	Approved
0.6935	Remote Similarity	NPD8335	Approved
0.6935	Remote Similarity	NPD8380	Approved
0.6909	Remote Similarity	NPD6001	Approved
0.6909	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7900	Approved
0.6906	Remote Similarity	NPD7236	Approved
0.6887	Remote Similarity	NPD4623	Approved
0.6887	Remote Similarity	NPD4519	Discontinued
0.6881	Remote Similarity	NPD8035	Phase 2
0.6881	Remote Similarity	NPD5694	Approved
0.6881	Remote Similarity	NPD8034	Phase 2
0.6881	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD6033	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