NPASS Compound

Structure

NPC60681 OpenBabel07101718312D 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 -3.4641 1.0000 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 -1.7321 3.0000 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 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 1.5000 0.0000 C 0 0 2 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 -0.8660 2.5000 0.0000 C 0 0 0 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 -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 -0.8660 1.5000 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 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 16 1 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 10 1 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 16 2 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 27 1 0 0 0 0 15 23 1 0 0 0 0 15 28 1 0 0 0 0 17 11 1 1 0 0 0 17 35 1 0 0 0 0 18 19 1 0 0 0 0 18 30 1 6 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 20 31 2 0 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 26 1 0 0 0 0 22 32 1 6 0 0 0 23 30 1 0 0 0 0 23 33 2 0 0 0 0 24 27 1 1 0 0 0 24 30 1 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:	470.34
Volume:	505.985
LogP:	4.102
LogD:	3.781
LogS:	-3.906
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	5.431
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:	-5.483
MDCK Permeability:	1.0488625775906257e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	90.02665710449219%
Volume Distribution (VD):	0.55
Pgp-substrate:	7.118693828582764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.329
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	1.559
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.694
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.626
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.079
Carcinogencity:	0.037
Eye Corrosion:	0.098
Eye Irritation:	0.152
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC60681

Natural Product ID:	NPC60681
*Common Name:**	Elaeocarpucin H
IUPAC Name:	n.a.
Synonyms:	Elaeocarpucin H
Standard InCHIKey:	KYAJJIYYRHRDHS-AOPDKZAKSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-16(2)11-17-13-29(7,34)25-21(35-17)14-27(5)24-20(31)12-19-18(9-10-22(32)26(19,3)4)30(24,8)23(33)15-28(25,27)6/h11-12,17-18,21-22,24-25,32,34H,9-10,13-15H2,1-8H3/t17-,18+,21+,22-,24-,25-,27-,28+,29-,30+/m0/s1
SMILES:	CC(=C[C@@H]1O[C@@H]2C[C@@]3([C@]([C@H]2[C@@](C1)(C)O)(C)CC(=O)[C@@]1([C@H]3C(=O)C=C2[C@H]1CC[C@@H](C2(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022240
PubChem CID:	57379943
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	=	2700.0	nM	PMID[548471]

☑ 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 NPC60681 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	210
0.1-0.2	1306
0.2-0.3	4263
0.3-0.4	9085
0.4-0.5	12304
0.5-0.6	6460
0.6-0.7	5829
0.7-0.8	2986
0.8-0.85	237
0.85-0.9	11
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC185530
0.96	High Similarity	NPC177064
0.9592	High Similarity	NPC26478
0.9307	High Similarity	NPC144459
0.9091	High Similarity	NPC83709
0.8922	High Similarity	NPC137657
0.8922	High Similarity	NPC75531
0.8922	High Similarity	NPC149124
0.8687	High Similarity	NPC472932
0.8627	High Similarity	NPC474327
0.8571	High Similarity	NPC185
0.8557	High Similarity	NPC1015
0.8557	High Similarity	NPC31985
0.8544	High Similarity	NPC477915
0.8544	High Similarity	NPC473424
0.8544	High Similarity	NPC87351
0.8519	High Similarity	NPC475524
0.8519	High Similarity	NPC100267
0.8515	High Similarity	NPC151488
0.8515	High Similarity	NPC18509
0.8485	Intermediate Similarity	NPC472930
0.8476	Intermediate Similarity	NPC478052
0.8476	Intermediate Similarity	NPC149047
0.8469	Intermediate Similarity	NPC48010
0.8468	Intermediate Similarity	NPC257457
0.8468	Intermediate Similarity	NPC311554
0.8462	Intermediate Similarity	NPC236390
0.8462	Intermediate Similarity	NPC311612
0.8416	Intermediate Similarity	NPC471463
0.8416	Intermediate Similarity	NPC249954
0.8411	Intermediate Similarity	NPC214644
0.8396	Intermediate Similarity	NPC477916
0.8396	Intermediate Similarity	NPC475294
0.8396	Intermediate Similarity	NPC220229
0.8396	Intermediate Similarity	NPC475060
0.8396	Intermediate Similarity	NPC83744
0.8393	Intermediate Similarity	NPC475041
0.8384	Intermediate Similarity	NPC472975
0.8381	Intermediate Similarity	NPC209502
0.8381	Intermediate Similarity	NPC204833
0.8378	Intermediate Similarity	NPC476965
0.8378	Intermediate Similarity	NPC470959
0.8367	Intermediate Similarity	NPC477943
0.8365	Intermediate Similarity	NPC204450
0.8365	Intermediate Similarity	NPC195290
0.8351	Intermediate Similarity	NPC475740
0.835	Intermediate Similarity	NPC154072
0.835	Intermediate Similarity	NPC144956
0.8349	Intermediate Similarity	NPC207251
0.8349	Intermediate Similarity	NPC221144
0.8349	Intermediate Similarity	NPC476163
0.8333	Intermediate Similarity	NPC291634
0.8333	Intermediate Similarity	NPC126815
0.8333	Intermediate Similarity	NPC190554
0.8333	Intermediate Similarity	NPC76084
0.8318	Intermediate Similarity	NPC217201
0.8318	Intermediate Similarity	NPC329417
0.8317	Intermediate Similarity	NPC469599
0.8317	Intermediate Similarity	NPC473170
0.8317	Intermediate Similarity	NPC259286
0.8304	Intermediate Similarity	NPC329736
0.8302	Intermediate Similarity	NPC49958
0.8302	Intermediate Similarity	NPC85829
0.8302	Intermediate Similarity	NPC97202
0.8302	Intermediate Similarity	NPC476027
0.8302	Intermediate Similarity	NPC171137
0.8302	Intermediate Similarity	NPC50692
0.8302	Intermediate Similarity	NPC302607
0.8302	Intermediate Similarity	NPC202167
0.8302	Intermediate Similarity	NPC214264
0.8302	Intermediate Similarity	NPC48733
0.8302	Intermediate Similarity	NPC150531
0.8302	Intermediate Similarity	NPC319077
0.8302	Intermediate Similarity	NPC296945
0.8302	Intermediate Similarity	NPC257353
0.8302	Intermediate Similarity	NPC260268
0.8302	Intermediate Similarity	NPC152695
0.83	Intermediate Similarity	NPC69454
0.8288	Intermediate Similarity	NPC148458
0.8286	Intermediate Similarity	NPC112009
0.8286	Intermediate Similarity	NPC111323
0.8283	Intermediate Similarity	NPC320026
0.8273	Intermediate Similarity	NPC122056
0.8273	Intermediate Similarity	NPC317210
0.8269	Intermediate Similarity	NPC473174
0.8265	Intermediate Similarity	NPC328539
0.8261	Intermediate Similarity	NPC204812
0.8261	Intermediate Similarity	NPC473979
0.8257	Intermediate Similarity	NPC43775
0.8252	Intermediate Similarity	NPC197386
0.8252	Intermediate Similarity	NPC471784
0.8252	Intermediate Similarity	NPC176845
0.8252	Intermediate Similarity	NPC303777
0.8247	Intermediate Similarity	NPC474732
0.8247	Intermediate Similarity	NPC474778
0.8247	Intermediate Similarity	NPC474733
0.8247	Intermediate Similarity	NPC31564
0.8247	Intermediate Similarity	NPC145879
0.8241	Intermediate Similarity	NPC11710
0.8235	Intermediate Similarity	NPC328371
0.8235	Intermediate Similarity	NPC160056
0.823	Intermediate Similarity	NPC473270
0.823	Intermediate Similarity	NPC264954
0.823	Intermediate Similarity	NPC476960
0.823	Intermediate Similarity	NPC61520
0.8224	Intermediate Similarity	NPC44063
0.8224	Intermediate Similarity	NPC220974
0.8218	Intermediate Similarity	NPC111015
0.8218	Intermediate Similarity	NPC8993
0.8214	Intermediate Similarity	NPC471854
0.8214	Intermediate Similarity	NPC239273
0.82	Intermediate Similarity	NPC475806
0.82	Intermediate Similarity	NPC472978
0.82	Intermediate Similarity	NPC168027
0.82	Intermediate Similarity	NPC473998
0.82	Intermediate Similarity	NPC185936
0.82	Intermediate Similarity	NPC63748
0.8198	Intermediate Similarity	NPC470953
0.8198	Intermediate Similarity	NPC147912
0.8198	Intermediate Similarity	NPC67259
0.8198	Intermediate Similarity	NPC326542
0.819	Intermediate Similarity	NPC155332
0.819	Intermediate Similarity	NPC114540
0.819	Intermediate Similarity	NPC56498
0.819	Intermediate Similarity	NPC32868
0.819	Intermediate Similarity	NPC32577
0.819	Intermediate Similarity	NPC136289
0.819	Intermediate Similarity	NPC22388
0.819	Intermediate Similarity	NPC241456
0.8182	Intermediate Similarity	NPC309603
0.8182	Intermediate Similarity	NPC76879
0.8182	Intermediate Similarity	NPC2983
0.8182	Intermediate Similarity	NPC474245
0.8182	Intermediate Similarity	NPC326627
0.8182	Intermediate Similarity	NPC473999
0.8182	Intermediate Similarity	NPC86319
0.8182	Intermediate Similarity	NPC310010
0.8182	Intermediate Similarity	NPC186688
0.8182	Intermediate Similarity	NPC32830
0.8182	Intermediate Similarity	NPC191620
0.8182	Intermediate Similarity	NPC275740
0.8174	Intermediate Similarity	NPC269642
0.8173	Intermediate Similarity	NPC15390
0.8173	Intermediate Similarity	NPC205899
0.8173	Intermediate Similarity	NPC473176
0.8165	Intermediate Similarity	NPC197428
0.8165	Intermediate Similarity	NPC37116
0.8163	Intermediate Similarity	NPC317590
0.8163	Intermediate Similarity	NPC58063
0.8158	Intermediate Similarity	NPC79579
0.8158	Intermediate Similarity	NPC476962
0.8158	Intermediate Similarity	NPC474370
0.8158	Intermediate Similarity	NPC476961
0.8155	Intermediate Similarity	NPC18319
0.8155	Intermediate Similarity	NPC253826
0.8155	Intermediate Similarity	NPC69385
0.8148	Intermediate Similarity	NPC65941
0.8148	Intermediate Similarity	NPC472825
0.8144	Intermediate Similarity	NPC469948
0.8142	Intermediate Similarity	NPC153440
0.8137	Intermediate Similarity	NPC318282
0.8137	Intermediate Similarity	NPC470016
0.8137	Intermediate Similarity	NPC316215
0.8137	Intermediate Similarity	NPC469995
0.8137	Intermediate Similarity	NPC173875
0.8137	Intermediate Similarity	NPC174948
0.8137	Intermediate Similarity	NPC317586
0.8137	Intermediate Similarity	NPC271195
0.8136	Intermediate Similarity	NPC311534
0.8131	Intermediate Similarity	NPC278628
0.8131	Intermediate Similarity	NPC231530
0.8125	Intermediate Similarity	NPC190286
0.8125	Intermediate Similarity	NPC469794
0.8125	Intermediate Similarity	NPC72772
0.8125	Intermediate Similarity	NPC270929
0.8119	Intermediate Similarity	NPC472942
0.8113	Intermediate Similarity	NPC180204
0.8113	Intermediate Similarity	NPC191892
0.8113	Intermediate Similarity	NPC249187
0.8113	Intermediate Similarity	NPC247957
0.8108	Intermediate Similarity	NPC108721
0.8108	Intermediate Similarity	NPC250109
0.8108	Intermediate Similarity	NPC962
0.8108	Intermediate Similarity	NPC194100
0.8108	Intermediate Similarity	NPC73300
0.8108	Intermediate Similarity	NPC73050
0.81	Intermediate Similarity	NPC171441
0.8095	Intermediate Similarity	NPC81530
0.8095	Intermediate Similarity	NPC476897
0.8095	Intermediate Similarity	NPC472637
0.8095	Intermediate Similarity	NPC310981
0.8091	Intermediate Similarity	NPC474315
0.8091	Intermediate Similarity	NPC470960
0.8087	Intermediate Similarity	NPC473256
0.8087	Intermediate Similarity	NPC46570
0.8087	Intermediate Similarity	NPC470878
0.8081	Intermediate Similarity	NPC471722
0.8081	Intermediate Similarity	NPC131470
0.8081	Intermediate Similarity	NPC53911
0.8081	Intermediate Similarity	NPC143767

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 NPC60681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1508
0.2-0.3	3793
0.3-0.4	2433
0.4-0.5	739
0.5-0.6	167
0.6-0.7	161
0.7-0.8	130
0.8-0.85	46
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8515	High Similarity	NPD4755	Approved
0.8476	Intermediate Similarity	NPD6675	Approved
0.8476	Intermediate Similarity	NPD6402	Approved
0.8476	Intermediate Similarity	NPD5739	Approved
0.8476	Intermediate Similarity	NPD7128	Approved
0.8411	Intermediate Similarity	NPD6373	Approved
0.8411	Intermediate Similarity	NPD6372	Approved
0.8367	Intermediate Similarity	NPD5328	Approved
0.8365	Intermediate Similarity	NPD5211	Phase 2
0.835	Intermediate Similarity	NPD5286	Approved
0.835	Intermediate Similarity	NPD4696	Approved
0.835	Intermediate Similarity	NPD4700	Approved
0.835	Intermediate Similarity	NPD5285	Approved
0.8318	Intermediate Similarity	NPD6899	Approved
0.8318	Intermediate Similarity	NPD6881	Approved
0.8318	Intermediate Similarity	NPD7320	Approved
0.8257	Intermediate Similarity	NPD6649	Approved
0.8257	Intermediate Similarity	NPD6650	Approved
0.8224	Intermediate Similarity	NPD5697	Approved
0.8224	Intermediate Similarity	NPD5701	Approved
0.8208	Intermediate Similarity	NPD5141	Approved
0.82	Intermediate Similarity	NPD6079	Approved
0.819	Intermediate Similarity	NPD5224	Approved
0.819	Intermediate Similarity	NPD5226	Approved
0.819	Intermediate Similarity	NPD4633	Approved
0.819	Intermediate Similarity	NPD5225	Approved
0.8182	Intermediate Similarity	NPD4753	Phase 2
0.8165	Intermediate Similarity	NPD7290	Approved
0.8165	Intermediate Similarity	NPD6883	Approved
0.8165	Intermediate Similarity	NPD7102	Approved
0.8155	Intermediate Similarity	NPD6084	Phase 2
0.8155	Intermediate Similarity	NPD6083	Phase 2
0.8119	Intermediate Similarity	NPD4202	Approved
0.8113	Intermediate Similarity	NPD5175	Approved
0.8113	Intermediate Similarity	NPD5174	Approved
0.8095	Intermediate Similarity	NPD5223	Approved
0.8091	Intermediate Similarity	NPD6617	Approved
0.8091	Intermediate Similarity	NPD8130	Phase 1
0.8091	Intermediate Similarity	NPD6869	Approved
0.8091	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD6012	Approved
0.8073	Intermediate Similarity	NPD6013	Approved
0.8073	Intermediate Similarity	NPD6014	Approved
0.8058	Intermediate Similarity	NPD4697	Phase 3
0.8053	Intermediate Similarity	NPD7115	Discovery
0.8041	Intermediate Similarity	NPD3133	Approved
0.8041	Intermediate Similarity	NPD3666	Approved
0.8041	Intermediate Similarity	NPD4786	Approved
0.8041	Intermediate Similarity	NPD3665	Phase 1
0.8018	Intermediate Similarity	NPD8297	Approved
0.8018	Intermediate Similarity	NPD6882	Approved
0.7982	Intermediate Similarity	NPD6011	Approved
0.7963	Intermediate Similarity	NPD4767	Approved
0.7963	Intermediate Similarity	NPD4768	Approved
0.7944	Intermediate Similarity	NPD4754	Approved
0.7941	Intermediate Similarity	NPD6399	Phase 3
0.7928	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7638	Approved
0.7885	Intermediate Similarity	NPD5221	Approved
0.7885	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5222	Approved
0.7879	Intermediate Similarity	NPD3618	Phase 1
0.7835	Intermediate Similarity	NPD4221	Approved
0.7835	Intermediate Similarity	NPD3667	Approved
0.7835	Intermediate Similarity	NPD4223	Phase 3
0.783	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD7640	Approved
0.7818	Intermediate Similarity	NPD4730	Approved
0.7818	Intermediate Similarity	NPD5128	Approved
0.7818	Intermediate Similarity	NPD4729	Approved
0.7815	Intermediate Similarity	NPD7507	Approved
0.781	Intermediate Similarity	NPD5173	Approved
0.7788	Intermediate Similarity	NPD5210	Approved
0.7788	Intermediate Similarity	NPD4629	Approved
0.7788	Intermediate Similarity	NPD5695	Phase 3
0.7778	Intermediate Similarity	NPD5329	Approved
0.7736	Intermediate Similarity	NPD5696	Approved
0.7727	Intermediate Similarity	NPD6412	Phase 2
0.7723	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6684	Approved
0.77	Intermediate Similarity	NPD7334	Approved
0.77	Intermediate Similarity	NPD7146	Approved
0.77	Intermediate Similarity	NPD6409	Approved
0.77	Intermediate Similarity	NPD7521	Approved
0.77	Intermediate Similarity	NPD5330	Approved
0.7699	Intermediate Similarity	NPD6053	Discontinued
0.7679	Intermediate Similarity	NPD5250	Approved
0.7679	Intermediate Similarity	NPD4634	Approved
0.7679	Intermediate Similarity	NPD5249	Phase 3
0.7679	Intermediate Similarity	NPD5248	Approved
0.7679	Intermediate Similarity	NPD5247	Approved
0.7679	Intermediate Similarity	NPD5251	Approved
0.7677	Intermediate Similarity	NPD4197	Approved
0.767	Intermediate Similarity	NPD5693	Phase 1
0.7652	Intermediate Similarity	NPD6274	Approved
0.7636	Intermediate Similarity	NPD6008	Approved
0.7623	Intermediate Similarity	NPD7319	Approved
0.7611	Intermediate Similarity	NPD5217	Approved
0.7611	Intermediate Similarity	NPD5215	Approved
0.7611	Intermediate Similarity	NPD5216	Approved
0.7607	Intermediate Similarity	NPD7101	Approved
0.7607	Intermediate Similarity	NPD7100	Approved
0.7549	Intermediate Similarity	NPD6903	Approved
0.7542	Intermediate Similarity	NPD6054	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7525	Intermediate Similarity	NPD5205	Approved
0.7525	Intermediate Similarity	NPD4689	Approved
0.7525	Intermediate Similarity	NPD4690	Approved
0.7525	Intermediate Similarity	NPD4688	Approved
0.7525	Intermediate Similarity	NPD4693	Phase 3
0.7525	Intermediate Similarity	NPD4138	Approved
0.7524	Intermediate Similarity	NPD7748	Approved
0.7522	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5135	Approved
0.7522	Intermediate Similarity	NPD5169	Approved
0.7521	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.7479	Intermediate Similarity	NPD6908	Approved
0.7479	Intermediate Similarity	NPD6909	Approved
0.7478	Intermediate Similarity	NPD4632	Approved
0.7477	Intermediate Similarity	NPD7902	Approved
0.7476	Intermediate Similarity	NPD6080	Approved
0.7476	Intermediate Similarity	NPD6673	Approved
0.7476	Intermediate Similarity	NPD6904	Approved
0.7456	Intermediate Similarity	NPD5127	Approved
0.7453	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6317	Approved
0.7417	Intermediate Similarity	NPD6370	Approved
0.74	Intermediate Similarity	NPD4788	Approved
0.7395	Intermediate Similarity	NPD6319	Approved
0.7379	Intermediate Similarity	NPD5737	Approved
0.7379	Intermediate Similarity	NPD6672	Approved
0.7373	Intermediate Similarity	NPD6314	Approved
0.7373	Intermediate Similarity	NPD6313	Approved
0.7353	Intermediate Similarity	NPD5690	Phase 2
0.7353	Intermediate Similarity	NPD4694	Approved
0.7353	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5280	Approved
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.7333	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD6016	Approved
0.7327	Intermediate Similarity	NPD3668	Phase 3
0.7308	Intermediate Similarity	NPD6051	Approved
0.7295	Intermediate Similarity	NPD7492	Approved
0.7288	Intermediate Similarity	NPD6009	Approved
0.7282	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD5988	Approved
0.7265	Intermediate Similarity	NPD5167	Approved
0.7258	Intermediate Similarity	NPD7736	Approved
0.7236	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD7327	Approved
0.7227	Intermediate Similarity	NPD7328	Approved
0.7216	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7604	Phase 2
0.7212	Intermediate Similarity	NPD5208	Approved
0.7207	Intermediate Similarity	NPD7632	Discontinued
0.7203	Intermediate Similarity	NPD6868	Approved
0.7196	Intermediate Similarity	NPD7900	Approved
0.7196	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5168	Approved
0.719	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5983	Phase 2
0.719	Intermediate Similarity	NPD8033	Approved
0.7184	Intermediate Similarity	NPD6098	Approved
0.7177	Intermediate Similarity	NPD7078	Approved
0.7177	Intermediate Similarity	NPD8293	Discontinued
0.7172	Intermediate Similarity	NPD4195	Approved
0.717	Intermediate Similarity	NPD5284	Approved
0.717	Intermediate Similarity	NPD8034	Phase 2
0.717	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD8035	Phase 2
0.717	Intermediate Similarity	NPD5281	Approved
0.7167	Intermediate Similarity	NPD7516	Approved
0.7115	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7339	Approved
0.7113	Intermediate Similarity	NPD6942	Approved
0.7107	Intermediate Similarity	NPD8377	Approved
0.7107	Intermediate Similarity	NPD8294	Approved
0.71	Intermediate Similarity	NPD7525	Registered
0.7097	Intermediate Similarity	NPD6336	Discontinued
0.7091	Intermediate Similarity	NPD4225	Approved
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5692	Phase 3
0.7075	Intermediate Similarity	NPD5785	Approved
0.7049	Intermediate Similarity	NPD8296	Approved
0.7049	Intermediate Similarity	NPD8380	Approved
0.7049	Intermediate Similarity	NPD8335	Approved
0.7049	Intermediate Similarity	NPD7503	Approved
0.7049	Intermediate Similarity	NPD8378	Approved
0.7049	Intermediate Similarity	NPD8379	Approved
0.7043	Intermediate Similarity	NPD6686	Approved
0.7037	Intermediate Similarity	NPD6001	Approved
0.7019	Intermediate Similarity	NPD4623	Approved
0.7019	Intermediate Similarity	NPD4519	Discontinued
0.7009	Intermediate Similarity	NPD5694	Approved
0.7009	Intermediate Similarity	NPD6411	Approved
0.6984	Remote Similarity	NPD6033	Approved
0.6983	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4695	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data