NPASS Compound

Structure

NPC137657 OpenBabel07101719132D 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 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 5.1962 -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 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 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:	484.32
Volume:	518.059
LogP:	4.306
LogD:	3.531
LogS:	-4.715
# 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:	0.435
Synthetic Accessibility Score:	5.494
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.914
MDCK Permeability:	2.0828310880460776e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.783
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.945
Plasma Protein Binding (PPB):	75.8650894165039%
Volume Distribution (VD):	1.545
Pgp-substrate:	17.33649444580078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.625

ADMET: Excretion

Clearance (CL):	9.124
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.399
Carcinogencity:	0.724
Eye Corrosion:	0.009
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: NPC137657

Natural Product ID:	NPC137657
*Common Name:**	Elaeocarpucin D
IUPAC Name:	n.a.
Synonyms:	Elaeocarpucin D
Standard InCHIKey:	XUMSZWVXRFLQPC-MCSCLXEZSA-N
Standard InCHI:	InChI=1S/C30H44O5/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/h9,18-22,25,31,34H,1,10-15H2,2-8H3/t18-,19-,20-,21+,22+,25+,27+,28-,29+,30+/m1/s1
SMILES:	C=C(C)C(=O)[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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023379
PubChem CID:	57379697
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	=	5600.0	nM	PMID[533166]

☑ 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 NPC137657 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	212
0.1-0.2	1360
0.2-0.3	5203
0.3-0.4	11281
0.4-0.5	10145
0.5-0.6	6262
0.6-0.7	5433
0.7-0.8	2563
0.8-0.85	206
0.85-0.9	29
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9184	High Similarity	NPC83709
0.9	High Similarity	NPC185530
0.8932	High Similarity	NPC177064
0.8922	High Similarity	NPC60681
0.8911	High Similarity	NPC26478
0.8857	High Similarity	NPC43775
0.8835	High Similarity	NPC44063
0.8835	High Similarity	NPC185
0.8824	High Similarity	NPC149124
0.8824	High Similarity	NPC75531
0.8812	High Similarity	NPC87351
0.88	High Similarity	NPC144956
0.8788	High Similarity	NPC18509
0.8725	High Similarity	NPC311612
0.8725	High Similarity	NPC191892
0.8687	High Similarity	NPC49371
0.8667	High Similarity	NPC214644
0.8667	High Similarity	NPC2766
0.8654	High Similarity	NPC144459
0.8646	High Similarity	NPC474245
0.8646	High Similarity	NPC76879
0.8614	High Similarity	NPC474720
0.8614	High Similarity	NPC15390
0.8586	High Similarity	NPC469599
0.8544	High Similarity	NPC111323
0.8519	High Similarity	NPC202889
0.8476	Intermediate Similarity	NPC165873
0.8469	Intermediate Similarity	NPC168027
0.8469	Intermediate Similarity	NPC185936
0.8462	Intermediate Similarity	NPC235889
0.8455	Intermediate Similarity	NPC471854
0.8454	Intermediate Similarity	NPC326627
0.8454	Intermediate Similarity	NPC310010
0.8454	Intermediate Similarity	NPC477943
0.8454	Intermediate Similarity	NPC1015
0.8454	Intermediate Similarity	NPC31985
0.8426	Intermediate Similarity	NPC475524
0.8426	Intermediate Similarity	NPC280782
0.8426	Intermediate Similarity	NPC100267
0.8426	Intermediate Similarity	NPC71348
0.8416	Intermediate Similarity	NPC190554
0.8396	Intermediate Similarity	NPC94529
0.8384	Intermediate Similarity	NPC233118
0.8381	Intermediate Similarity	NPC257353
0.8381	Intermediate Similarity	NPC181265
0.8381	Intermediate Similarity	NPC196528
0.8378	Intermediate Similarity	NPC257457
0.8378	Intermediate Similarity	NPC311554
0.8364	Intermediate Similarity	NPC270958
0.835	Intermediate Similarity	NPC474327
0.8349	Intermediate Similarity	NPC194100
0.8333	Intermediate Similarity	NPC20688
0.8333	Intermediate Similarity	NPC51014
0.8333	Intermediate Similarity	NPC214797
0.8333	Intermediate Similarity	NPC118860
0.8333	Intermediate Similarity	NPC231589
0.8318	Intermediate Similarity	NPC304495
0.8318	Intermediate Similarity	NPC241927
0.8318	Intermediate Similarity	NPC258543
0.8317	Intermediate Similarity	NPC192428
0.83	Intermediate Similarity	NPC196485
0.83	Intermediate Similarity	NPC245972
0.8269	Intermediate Similarity	NPC477915
0.8269	Intermediate Similarity	NPC136289
0.8269	Intermediate Similarity	NPC473424
0.8269	Intermediate Similarity	NPC163249
0.8265	Intermediate Similarity	NPC32830
0.8261	Intermediate Similarity	NPC475194
0.8257	Intermediate Similarity	NPC170487
0.8257	Intermediate Similarity	NPC221144
0.8252	Intermediate Similarity	NPC112167
0.8247	Intermediate Similarity	NPC475740
0.8241	Intermediate Similarity	NPC197428
0.8229	Intermediate Similarity	NPC474218
0.8218	Intermediate Similarity	NPC472932
0.8218	Intermediate Similarity	NPC473170
0.8214	Intermediate Similarity	NPC118638
0.8214	Intermediate Similarity	NPC329736
0.8208	Intermediate Similarity	NPC149047
0.8208	Intermediate Similarity	NPC278628
0.8208	Intermediate Similarity	NPC231530
0.8198	Intermediate Similarity	NPC148458
0.819	Intermediate Similarity	NPC249187
0.819	Intermediate Similarity	NPC179208
0.819	Intermediate Similarity	NPC247957
0.819	Intermediate Similarity	NPC117185
0.8182	Intermediate Similarity	NPC171441
0.8182	Intermediate Similarity	NPC108721
0.8182	Intermediate Similarity	NPC73300
0.8173	Intermediate Similarity	NPC81530
0.8163	Intermediate Similarity	NPC53911
0.8163	Intermediate Similarity	NPC328313
0.8163	Intermediate Similarity	NPC328539
0.8158	Intermediate Similarity	NPC470921
0.8155	Intermediate Similarity	NPC147954
0.8155	Intermediate Similarity	NPC477854
0.8148	Intermediate Similarity	NPC470257
0.8148	Intermediate Similarity	NPC41405
0.8144	Intermediate Similarity	NPC474732
0.8144	Intermediate Similarity	NPC31564
0.8144	Intermediate Similarity	NPC327115
0.8144	Intermediate Similarity	NPC145879
0.8144	Intermediate Similarity	NPC474778
0.8144	Intermediate Similarity	NPC474733
0.8142	Intermediate Similarity	NPC61520
0.8137	Intermediate Similarity	NPC328162
0.8137	Intermediate Similarity	NPC305483
0.8137	Intermediate Similarity	NPC96859
0.8131	Intermediate Similarity	NPC43285
0.8131	Intermediate Similarity	NPC58370
0.8131	Intermediate Similarity	NPC220974
0.8131	Intermediate Similarity	NPC475060
0.8131	Intermediate Similarity	NPC83744
0.8131	Intermediate Similarity	NPC475294
0.8131	Intermediate Similarity	NPC477916
0.8131	Intermediate Similarity	NPC220229
0.8125	Intermediate Similarity	NPC82902
0.8125	Intermediate Similarity	NPC221758
0.8125	Intermediate Similarity	NPC470959
0.8125	Intermediate Similarity	NPC59453
0.8125	Intermediate Similarity	NPC476965
0.8125	Intermediate Similarity	NPC239273
0.8119	Intermediate Similarity	NPC111015
0.8113	Intermediate Similarity	NPC209502
0.8113	Intermediate Similarity	NPC72255
0.8113	Intermediate Similarity	NPC204833
0.8113	Intermediate Similarity	NPC29705
0.8108	Intermediate Similarity	NPC473798
0.8103	Intermediate Similarity	NPC473255
0.81	Intermediate Similarity	NPC154101
0.81	Intermediate Similarity	NPC272746
0.8095	Intermediate Similarity	NPC271266
0.8095	Intermediate Similarity	NPC22388
0.8095	Intermediate Similarity	NPC308351
0.8095	Intermediate Similarity	NPC473928
0.8095	Intermediate Similarity	NPC477054
0.8091	Intermediate Similarity	NPC207251
0.8081	Intermediate Similarity	NPC186688
0.8081	Intermediate Similarity	NPC119416
0.8081	Intermediate Similarity	NPC86319
0.8081	Intermediate Similarity	NPC275740
0.8077	Intermediate Similarity	NPC472972
0.8077	Intermediate Similarity	NPC154072
0.8077	Intermediate Similarity	NPC110149
0.8073	Intermediate Similarity	NPC163314
0.8073	Intermediate Similarity	NPC76084
0.8073	Intermediate Similarity	NPC235077
0.8061	Intermediate Similarity	NPC472482
0.8061	Intermediate Similarity	NPC317590
0.8061	Intermediate Similarity	NPC472484
0.8061	Intermediate Similarity	NPC472481
0.8061	Intermediate Similarity	NPC174619
0.8061	Intermediate Similarity	NPC90652
0.8061	Intermediate Similarity	NPC58063
0.8058	Intermediate Similarity	NPC470834
0.8056	Intermediate Similarity	NPC217201
0.8056	Intermediate Similarity	NPC329417
0.8056	Intermediate Similarity	NPC65941
0.8051	Intermediate Similarity	NPC168899
0.8051	Intermediate Similarity	NPC293623
0.8051	Intermediate Similarity	NPC69273
0.8041	Intermediate Similarity	NPC469948
0.8039	Intermediate Similarity	NPC472485
0.8039	Intermediate Similarity	NPC470016
0.8039	Intermediate Similarity	NPC317586
0.8037	Intermediate Similarity	NPC265127
0.8037	Intermediate Similarity	NPC214264
0.8037	Intermediate Similarity	NPC475571
0.8037	Intermediate Similarity	NPC97202
0.8037	Intermediate Similarity	NPC48733
0.8037	Intermediate Similarity	NPC150531
0.8037	Intermediate Similarity	NPC476027
0.8037	Intermediate Similarity	NPC50692
0.8037	Intermediate Similarity	NPC319077
0.8037	Intermediate Similarity	NPC296945
0.8037	Intermediate Similarity	NPC202167
0.8037	Intermediate Similarity	NPC171137
0.8037	Intermediate Similarity	NPC152695
0.8037	Intermediate Similarity	NPC49958
0.8037	Intermediate Similarity	NPC260268
0.8037	Intermediate Similarity	NPC85829
0.8037	Intermediate Similarity	NPC302607
0.8036	Intermediate Similarity	NPC270929
0.8036	Intermediate Similarity	NPC328374
0.8036	Intermediate Similarity	NPC251236
0.8036	Intermediate Similarity	NPC96312
0.8036	Intermediate Similarity	NPC40632
0.8021	Intermediate Similarity	NPC476082
0.8021	Intermediate Similarity	NPC278648
0.802	Intermediate Similarity	NPC474807
0.802	Intermediate Similarity	NPC109414
0.802	Intermediate Similarity	NPC470376
0.802	Intermediate Similarity	NPC12722
0.802	Intermediate Similarity	NPC294263
0.802	Intermediate Similarity	NPC472930
0.802	Intermediate Similarity	NPC470375
0.8019	Intermediate Similarity	NPC236390
0.8019	Intermediate Similarity	NPC140723
0.8019	Intermediate Similarity	NPC275583
0.8019	Intermediate Similarity	NPC470839

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 NPC137657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1624
0.2-0.3	4098
0.3-0.4	2172
0.4-0.5	599
0.5-0.6	158
0.6-0.7	146
0.7-0.8	106
0.8-0.85	34
0.85-0.9	35
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8932	High Similarity	NPD6881	Approved
0.8932	High Similarity	NPD6899	Approved
0.8922	High Similarity	NPD6402	Approved
0.8922	High Similarity	NPD7128	Approved
0.8922	High Similarity	NPD6675	Approved
0.8922	High Similarity	NPD5739	Approved
0.8857	High Similarity	NPD6649	Approved
0.8857	High Similarity	NPD6650	Approved
0.8846	High Similarity	NPD6373	Approved
0.8846	High Similarity	NPD6372	Approved
0.8835	High Similarity	NPD5697	Approved
0.88	High Similarity	NPD5286	Approved
0.88	High Similarity	NPD4696	Approved
0.88	High Similarity	NPD5285	Approved
0.8788	High Similarity	NPD4755	Approved
0.8762	High Similarity	NPD7102	Approved
0.8762	High Similarity	NPD7290	Approved
0.8762	High Similarity	NPD6883	Approved
0.875	High Similarity	NPD7320	Approved
0.8679	High Similarity	NPD6617	Approved
0.8679	High Similarity	NPD8130	Phase 1
0.8679	High Similarity	NPD6869	Approved
0.8679	High Similarity	NPD6847	Approved
0.8667	High Similarity	NPD6013	Approved
0.8667	High Similarity	NPD6012	Approved
0.8667	High Similarity	NPD6014	Approved
0.8654	High Similarity	NPD5701	Approved
0.8627	High Similarity	NPD5224	Approved
0.8627	High Similarity	NPD5225	Approved
0.8627	High Similarity	NPD5226	Approved
0.8627	High Similarity	NPD4633	Approved
0.8627	High Similarity	NPD5211	Phase 2
0.8614	High Similarity	NPD4700	Approved
0.86	High Similarity	NPD6084	Phase 2
0.86	High Similarity	NPD6083	Phase 2
0.8598	High Similarity	NPD8297	Approved
0.8598	High Similarity	NPD6882	Approved
0.8571	High Similarity	NPD6011	Approved
0.8544	High Similarity	NPD5175	Approved
0.8544	High Similarity	NPD5174	Approved
0.8529	High Similarity	NPD5223	Approved
0.8462	Intermediate Similarity	NPD5141	Approved
0.8454	Intermediate Similarity	NPD4753	Phase 2
0.84	Intermediate Similarity	NPD5210	Approved
0.84	Intermediate Similarity	NPD4629	Approved
0.8333	Intermediate Similarity	NPD5696	Approved
0.8333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD5221	Approved
0.8317	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD5222	Approved
0.8317	Intermediate Similarity	NPD4697	Phase 3
0.8283	Intermediate Similarity	NPD6079	Approved
0.8265	Intermediate Similarity	NPD5328	Approved
0.8235	Intermediate Similarity	NPD5173	Approved
0.8224	Intermediate Similarity	NPD4730	Approved
0.8224	Intermediate Similarity	NPD5128	Approved
0.8224	Intermediate Similarity	NPD4729	Approved
0.8218	Intermediate Similarity	NPD5695	Phase 3
0.8208	Intermediate Similarity	NPD4768	Approved
0.8208	Intermediate Similarity	NPD4767	Approved
0.8198	Intermediate Similarity	NPD6274	Approved
0.819	Intermediate Similarity	NPD4754	Approved
0.8142	Intermediate Similarity	NPD7101	Approved
0.8142	Intermediate Similarity	NPD7100	Approved
0.8125	Intermediate Similarity	NPD4786	Approved
0.8073	Intermediate Similarity	NPD5250	Approved
0.8073	Intermediate Similarity	NPD5247	Approved
0.8073	Intermediate Similarity	NPD4634	Approved
0.8073	Intermediate Similarity	NPD5249	Phase 3
0.8073	Intermediate Similarity	NPD5251	Approved
0.8073	Intermediate Similarity	NPD5248	Approved
0.807	Intermediate Similarity	NPD6054	Approved
0.8053	Intermediate Similarity	NPD6335	Approved
0.8041	Intermediate Similarity	NPD5329	Approved
0.802	Intermediate Similarity	NPD6399	Phase 3
0.802	Intermediate Similarity	NPD4202	Approved
0.8	Intermediate Similarity	NPD5215	Approved
0.8	Intermediate Similarity	NPD5217	Approved
0.8	Intermediate Similarity	NPD5216	Approved
0.7965	Intermediate Similarity	NPD6317	Approved
0.7959	Intermediate Similarity	NPD3618	Phase 1
0.7938	Intermediate Similarity	NPD3666	Approved
0.7938	Intermediate Similarity	NPD3133	Approved
0.7938	Intermediate Similarity	NPD4197	Approved
0.7938	Intermediate Similarity	NPD3665	Phase 1
0.7931	Intermediate Similarity	NPD6370	Approved
0.7917	Intermediate Similarity	NPD3667	Approved
0.7913	Intermediate Similarity	NPD6319	Approved
0.7913	Intermediate Similarity	NPD6059	Approved
0.7909	Intermediate Similarity	NPD5169	Approved
0.7909	Intermediate Similarity	NPD5135	Approved
0.7909	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD6904	Approved
0.79	Intermediate Similarity	NPD6080	Approved
0.79	Intermediate Similarity	NPD6673	Approved
0.7895	Intermediate Similarity	NPD6314	Approved
0.7895	Intermediate Similarity	NPD6313	Approved
0.7857	Intermediate Similarity	NPD4632	Approved
0.7845	Intermediate Similarity	NPD6015	Approved
0.7845	Intermediate Similarity	NPD6909	Approved
0.7845	Intermediate Similarity	NPD6016	Approved
0.7845	Intermediate Similarity	NPD6908	Approved
0.7838	Intermediate Similarity	NPD5127	Approved
0.7807	Intermediate Similarity	NPD6009	Approved
0.78	Intermediate Similarity	NPD6672	Approved
0.78	Intermediate Similarity	NPD5737	Approved
0.7797	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD5690	Phase 2
0.7778	Intermediate Similarity	NPD5988	Approved
0.7778	Intermediate Similarity	NPD6098	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7732	Intermediate Similarity	NPD4223	Phase 3
0.7732	Intermediate Similarity	NPD4221	Approved
0.7731	Intermediate Similarity	NPD6616	Approved
0.7719	Intermediate Similarity	NPD6868	Approved
0.7712	Intermediate Similarity	NPD7604	Phase 2
0.7706	Intermediate Similarity	NPD6008	Approved
0.7692	Intermediate Similarity	NPD5983	Phase 2
0.7692	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7078	Approved
0.7653	Intermediate Similarity	NPD4788	Approved
0.7652	Intermediate Similarity	NPD7115	Discovery
0.7636	Intermediate Similarity	NPD6412	Phase 2
0.7632	Intermediate Similarity	NPD5167	Approved
0.7624	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6684	Approved
0.76	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7334	Approved
0.76	Intermediate Similarity	NPD7146	Approved
0.76	Intermediate Similarity	NPD6409	Approved
0.76	Intermediate Similarity	NPD5280	Approved
0.76	Intermediate Similarity	NPD4694	Approved
0.76	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD7521	Approved
0.76	Intermediate Similarity	NPD5330	Approved
0.7583	Intermediate Similarity	NPD6336	Discontinued
0.7573	Intermediate Similarity	NPD5693	Phase 1
0.7573	Intermediate Similarity	NPD6050	Approved
0.7568	Intermediate Similarity	NPD5168	Approved
0.7524	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD8293	Discontinued
0.7476	Intermediate Similarity	NPD5692	Phase 3
0.7451	Intermediate Similarity	NPD6903	Approved
0.7429	Intermediate Similarity	NPD7748	Approved
0.7426	Intermediate Similarity	NPD4689	Approved
0.7426	Intermediate Similarity	NPD4138	Approved
0.7426	Intermediate Similarity	NPD4690	Approved
0.7426	Intermediate Similarity	NPD4688	Approved
0.7426	Intermediate Similarity	NPD4693	Phase 3
0.7426	Intermediate Similarity	NPD5205	Approved
0.7404	Intermediate Similarity	NPD7515	Phase 2
0.7404	Intermediate Similarity	NPD5694	Approved
0.74	Intermediate Similarity	NPD3668	Phase 3
0.7383	Intermediate Similarity	NPD7902	Approved
0.7353	Intermediate Similarity	NPD3573	Approved
0.7347	Intermediate Similarity	NPD4695	Discontinued
0.7317	Intermediate Similarity	NPD6033	Approved
0.7292	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5091	Approved
0.7245	Intermediate Similarity	NPD4195	Approved
0.7238	Intermediate Similarity	NPD5284	Approved
0.7238	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD8034	Phase 2
0.7238	Intermediate Similarity	NPD5281	Approved
0.7188	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7339	Approved
0.7172	Intermediate Similarity	NPD7525	Registered
0.7168	Intermediate Similarity	NPD6614	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7638	Approved
0.7154	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7131	Intermediate Similarity	NPD8328	Phase 3
0.7115	Intermediate Similarity	NPD5208	Approved
0.7103	Intermediate Similarity	NPD7900	Approved
0.7103	Intermediate Similarity	NPD6001	Approved
0.7103	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7640	Approved
0.7091	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD6411	Approved
0.7037	Intermediate Similarity	NPD5654	Approved
0.7009	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD5133	Approved
0.6984	Remote Similarity	NPD7319	Approved
0.6981	Remote Similarity	NPD5207	Approved
0.6942	Remote Similarity	NPD4522	Approved
0.6931	Remote Similarity	NPD4692	Approved
0.6931	Remote Similarity	NPD4139	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5959	Approved
0.6907	Remote Similarity	NPD4784	Approved
0.6907	Remote Similarity	NPD4785	Approved
0.69	Remote Similarity	NPD7645	Phase 2
0.6887	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD4243	Approved
0.6863	Remote Similarity	NPD6435	Approved
0.6857	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4096	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