NPASS Compound

Structure

CID80566 OpenBabel06191715422D 39 43 0 0 1 0 0 0 0 0999 V2000 -4.4847 -0.4553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6852 1.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0277 -0.6196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8463 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6927 -2.9318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5390 -2.4432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5390 2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0070 1.0836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 0.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5390 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8463 0.4886 0.0000 C 0 0 1 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 -2.5390 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0049 -0.6196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -2.4432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -3.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3854 -2.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 2.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 2.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8795 2.0525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9099 0.7096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 29 1 0 0 0 0 6 39 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 30 1 0 0 0 0 9 11 1 0 0 0 0 9 26 1 0 0 0 0 10 12 1 0 0 0 0 10 29 1 0 0 0 0 11 31 1 0 0 0 0 12 31 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 26 1 0 0 0 0 15 20 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 16 32 2 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 31 1 1 0 0 0 19 22 1 0 0 0 0 19 33 1 6 0 0 0 20 23 1 0 0 0 0 20 34 1 1 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 27 1 1 0 0 0 22 30 1 0 0 0 0 23 28 1 1 0 0 0 23 35 1 0 0 0 0 24 36 2 0 0 0 0 24 37 1 0 0 0 0 25 26 1 0 0 0 0 25 38 2 0 0 0 0 25 39 1 0 0 0 0 26 1 1 6 0 0 0 27 2 1 1 0 0 0 28 3 1 1 0 0 0 29 30 1 1 0 0 0 30 5 1 1 0 0 0 31 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.32
Volume:	561.726
LogP:	1.68
LogD:	2.311
LogS:	-3.597
# Rotatable Bonds:	4
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.239
Synthetic Accessibility Score:	5.436
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.615
MDCK Permeability:	5.4190536502574105e-06
Pgp-inhibitor:	0.073
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.201
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.846
Plasma Protein Binding (PPB):	57.903114318847656%
Volume Distribution (VD):	0.467
Pgp-substrate:	22.99884033203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.637
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	1.704
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.067
Carcinogencity:	0.357
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC80566

Natural Product ID:	NPC80566
*Common Name:**	Olean-12-En-23-Al-2 Beta,3 Beta,11Alpha-Trihydroxy-30-Methoxycarbonyl-28-Oic Acid
IUPAC Name:	(2S,4aR,6aR,6aS,6bR,8aR,9S,10R,11S,12aS,13R,14bR)-9-formyl-10,11,13-trihydroxy-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	acinospesigenin-C
Standard InCHIKey:	HZHAFXOYSFFNOQ-VDJWNIPJSA-N
Standard InCHI:	InChI=1S/C31H46O8/c1-26(25(38)39-6)9-11-31(24(36)37)12-10-29(4)17(18(31)14-26)13-19(33)22-27(2)15-20(34)23(35)28(3,16-32)21(27)7-8-30(22,29)5/h13,16,18-23,33-35H,7-12,14-15H2,1-6H3,(H,36,37)/t18-,19-,20+,21-,22-,23+,26+,27+,28+,29-,30-,31+/m1/s1
SMILES:	COC(=O)[C@@]1(C)CC[C@]2([C@H](C1)C1=C[C@@H](O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)C[C@H](O)[C@@H]([C@@]1(C)C=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455058
PubChem CID:	11763315
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	10.0	mg.kg-1	PMID[493048]

☑ 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 NPC80566 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	235
0.1-0.2	1451
0.2-0.3	4370
0.3-0.4	9671
0.4-0.5	12731
0.5-0.6	6602
0.6-0.7	5111
0.7-0.8	2066
0.8-0.85	352
0.85-0.9	102
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC188833
0.8889	High Similarity	NPC43686
0.8889	High Similarity	NPC261935
0.8889	High Similarity	NPC106112
0.8866	High Similarity	NPC298554
0.8866	High Similarity	NPC136313
0.8866	High Similarity	NPC307335
0.8866	High Similarity	NPC74855
0.88	High Similarity	NPC29765
0.88	High Similarity	NPC111214
0.88	High Similarity	NPC271614
0.8788	High Similarity	NPC25848
0.8788	High Similarity	NPC19376
0.8788	High Similarity	NPC307282
0.8788	High Similarity	NPC305464
0.8788	High Similarity	NPC201657
0.8776	High Similarity	NPC209868
0.8776	High Similarity	NPC222047
0.8776	High Similarity	NPC87095
0.8763	High Similarity	NPC84319
0.8763	High Similarity	NPC235884
0.8763	High Similarity	NPC52021
0.8763	High Similarity	NPC71074
0.8763	High Similarity	NPC300351
0.8763	High Similarity	NPC472149
0.8763	High Similarity	NPC306541
0.8763	High Similarity	NPC25299
0.8713	High Similarity	NPC35239
0.87	High Similarity	NPC187933
0.87	High Similarity	NPC255589
0.87	High Similarity	NPC259788
0.8687	High Similarity	NPC96916
0.8673	High Similarity	NPC275809
0.866	High Similarity	NPC49320
0.8627	High Similarity	NPC256247
0.8614	High Similarity	NPC174663
0.86	High Similarity	NPC230151
0.86	High Similarity	NPC259733
0.86	High Similarity	NPC73004
0.86	High Similarity	NPC207922
0.86	High Similarity	NPC158371
0.86	High Similarity	NPC173744
0.86	High Similarity	NPC204961
0.8586	High Similarity	NPC88116
0.8586	High Similarity	NPC91010
0.8586	High Similarity	NPC32407
0.8586	High Similarity	NPC263548
0.8586	High Similarity	NPC282395
0.8586	High Similarity	NPC20235
0.8586	High Similarity	NPC299996
0.8586	High Similarity	NPC231063
0.8586	High Similarity	NPC145667
0.8571	High Similarity	NPC155120
0.8571	High Similarity	NPC301666
0.8571	High Similarity	NPC288833
0.8571	High Similarity	NPC228784
0.8571	High Similarity	NPC324341
0.8571	High Similarity	NPC966
0.8571	High Similarity	NPC282616
0.8558	High Similarity	NPC475036
0.8532	High Similarity	NPC110861
0.8515	High Similarity	NPC9613
0.8515	High Similarity	NPC247139
0.8515	High Similarity	NPC189880
0.85	High Similarity	NPC23241
0.85	High Similarity	NPC53565
0.85	High Similarity	NPC290481
0.85	High Similarity	NPC474727
0.85	High Similarity	NPC198245
0.8485	Intermediate Similarity	NPC133579
0.8485	Intermediate Similarity	NPC474806
0.8476	Intermediate Similarity	NPC477877
0.8469	Intermediate Similarity	NPC120968
0.8469	Intermediate Similarity	NPC172361
0.8469	Intermediate Similarity	NPC290614
0.8469	Intermediate Similarity	NPC291028
0.8469	Intermediate Similarity	NPC18872
0.8469	Intermediate Similarity	NPC477872
0.8469	Intermediate Similarity	NPC210037
0.8469	Intermediate Similarity	NPC7260
0.8469	Intermediate Similarity	NPC273621
0.8469	Intermediate Similarity	NPC227467
0.8469	Intermediate Similarity	NPC86372
0.8462	Intermediate Similarity	NPC95899
0.8455	Intermediate Similarity	NPC268954
0.8454	Intermediate Similarity	NPC40552
0.8454	Intermediate Similarity	NPC246708
0.8454	Intermediate Similarity	NPC52169
0.8454	Intermediate Similarity	NPC182797
0.8447	Intermediate Similarity	NPC54909
0.8447	Intermediate Similarity	NPC233012
0.8431	Intermediate Similarity	NPC164349
0.8431	Intermediate Similarity	NPC471966
0.8416	Intermediate Similarity	NPC98874
0.8416	Intermediate Similarity	NPC132824
0.8416	Intermediate Similarity	NPC116457
0.84	Intermediate Similarity	NPC188102
0.84	Intermediate Similarity	NPC159365
0.84	Intermediate Similarity	NPC296164
0.84	Intermediate Similarity	NPC474529
0.84	Intermediate Similarity	NPC184006
0.84	Intermediate Similarity	NPC23621
0.84	Intermediate Similarity	NPC78580
0.8384	Intermediate Similarity	NPC187722
0.8384	Intermediate Similarity	NPC6255
0.8384	Intermediate Similarity	NPC475708
0.8384	Intermediate Similarity	NPC471588
0.8384	Intermediate Similarity	NPC105189
0.8381	Intermediate Similarity	NPC284865
0.8367	Intermediate Similarity	NPC470588
0.8367	Intermediate Similarity	NPC234346
0.8367	Intermediate Similarity	NPC281524
0.8367	Intermediate Similarity	NPC225585
0.8367	Intermediate Similarity	NPC293048
0.8367	Intermediate Similarity	NPC143232
0.8367	Intermediate Similarity	NPC64872
0.8367	Intermediate Similarity	NPC290972
0.8367	Intermediate Similarity	NPC198664
0.8367	Intermediate Similarity	NPC274330
0.8367	Intermediate Similarity	NPC59263
0.8367	Intermediate Similarity	NPC130520
0.8367	Intermediate Similarity	NPC121798
0.8367	Intermediate Similarity	NPC263393
0.8367	Intermediate Similarity	NPC127689
0.8367	Intermediate Similarity	NPC270768
0.8367	Intermediate Similarity	NPC25906
0.8367	Intermediate Similarity	NPC61543
0.8351	Intermediate Similarity	NPC51700
0.8351	Intermediate Similarity	NPC242468
0.8351	Intermediate Similarity	NPC102683
0.8351	Intermediate Similarity	NPC142415
0.8351	Intermediate Similarity	NPC307426
0.8351	Intermediate Similarity	NPC171203
0.8351	Intermediate Similarity	NPC18064
0.8351	Intermediate Similarity	NPC98442
0.8351	Intermediate Similarity	NPC88716
0.8351	Intermediate Similarity	NPC293564
0.8351	Intermediate Similarity	NPC130577
0.8351	Intermediate Similarity	NPC68160
0.835	Intermediate Similarity	NPC476195
0.8349	Intermediate Similarity	NPC48249
0.8349	Intermediate Similarity	NPC100383
0.8333	Intermediate Similarity	NPC203343
0.8333	Intermediate Similarity	NPC476878
0.8333	Intermediate Similarity	NPC21728
0.8333	Intermediate Similarity	NPC476879
0.8333	Intermediate Similarity	NPC312075
0.8317	Intermediate Similarity	NPC195715
0.8317	Intermediate Similarity	NPC473240
0.8317	Intermediate Similarity	NPC148523
0.8317	Intermediate Similarity	NPC32118
0.83	Intermediate Similarity	NPC474436
0.83	Intermediate Similarity	NPC49776
0.83	Intermediate Similarity	NPC86368
0.83	Intermediate Similarity	NPC272075
0.83	Intermediate Similarity	NPC295643
0.83	Intermediate Similarity	NPC229281
0.83	Intermediate Similarity	NPC118519
0.83	Intermediate Similarity	NPC214756
0.83	Intermediate Similarity	NPC63118
0.83	Intermediate Similarity	NPC158059
0.83	Intermediate Similarity	NPC202728
0.8288	Intermediate Similarity	NPC44170
0.8286	Intermediate Similarity	NPC478057
0.8283	Intermediate Similarity	NPC470589
0.8283	Intermediate Similarity	NPC120840
0.8283	Intermediate Similarity	NPC474728
0.8283	Intermediate Similarity	NPC111110
0.8283	Intermediate Similarity	NPC126369
0.8283	Intermediate Similarity	NPC193750
0.8283	Intermediate Similarity	NPC130278
0.8283	Intermediate Similarity	NPC113989
0.8273	Intermediate Similarity	NPC238935
0.8273	Intermediate Similarity	NPC475208
0.8269	Intermediate Similarity	NPC96784
0.8269	Intermediate Similarity	NPC235920
0.8269	Intermediate Similarity	NPC476132
0.8265	Intermediate Similarity	NPC473242
0.8265	Intermediate Similarity	NPC474512
0.8265	Intermediate Similarity	NPC17733
0.8265	Intermediate Similarity	NPC470629
0.8265	Intermediate Similarity	NPC290690
0.8265	Intermediate Similarity	NPC181225
0.8257	Intermediate Similarity	NPC31839
0.8252	Intermediate Similarity	NPC58942
0.8252	Intermediate Similarity	NPC260149
0.8252	Intermediate Similarity	NPC247233
0.8247	Intermediate Similarity	NPC95594
0.8247	Intermediate Similarity	NPC235341
0.8247	Intermediate Similarity	NPC477579
0.8247	Intermediate Similarity	NPC72638
0.8241	Intermediate Similarity	NPC310546
0.8235	Intermediate Similarity	NPC327179
0.8235	Intermediate Similarity	NPC476318
0.8235	Intermediate Similarity	NPC476327
0.8218	Intermediate Similarity	NPC191412
0.8218	Intermediate Similarity	NPC470957
0.8218	Intermediate Similarity	NPC114159
0.8218	Intermediate Similarity	NPC148964
0.8218	Intermediate Similarity	NPC470958

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 NPC80566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1757
0.2-0.3	3740
0.3-0.4	2255
0.4-0.5	737
0.5-0.6	280
0.6-0.7	154
0.7-0.8	18
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.82	Intermediate Similarity	NPD7515	Phase 2
0.8039	Intermediate Similarity	NPD7748	Approved
0.7981	Intermediate Similarity	NPD7902	Approved
0.7692	Intermediate Similarity	NPD7900	Approved
0.7692	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7640	Approved
0.7664	Intermediate Similarity	NPD7639	Approved
0.7647	Intermediate Similarity	NPD8328	Phase 3
0.7589	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7115	Discovery
0.757	Intermediate Similarity	NPD7638	Approved
0.7426	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4225	Approved
0.7347	Intermediate Similarity	NPD7645	Phase 2
0.7339	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7264	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD5779	Approved
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7236	Intermediate Similarity	NPD7507	Approved
0.7193	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3618	Phase 1
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4697	Phase 3
0.7054	Intermediate Similarity	NPD7632	Discontinued
0.7043	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD6411	Approved
0.699	Remote Similarity	NPD4786	Approved
0.6983	Remote Similarity	NPD6373	Approved
0.6983	Remote Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD5328	Approved
0.6967	Remote Similarity	NPD6319	Approved
0.6961	Remote Similarity	NPD3667	Approved
0.6911	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD8517	Approved
0.6911	Remote Similarity	NPD8516	Approved
0.6911	Remote Similarity	NPD8513	Phase 3
0.6891	Remote Similarity	NPD8133	Approved
0.6891	Remote Similarity	NPD4632	Approved
0.6887	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6675	Approved
0.687	Remote Similarity	NPD6402	Approved
0.687	Remote Similarity	NPD5739	Approved
0.687	Remote Similarity	NPD7128	Approved
0.6864	Remote Similarity	NPD6649	Approved
0.6864	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.6852	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6412	Phase 2
0.6807	Remote Similarity	NPD8297	Approved
0.678	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD6899	Approved
0.6752	Remote Similarity	NPD7320	Approved
0.6752	Remote Similarity	NPD6881	Approved
0.6748	Remote Similarity	NPD7516	Approved
0.6733	Remote Similarity	NPD6114	Approved
0.6733	Remote Similarity	NPD6115	Approved
0.6733	Remote Similarity	NPD6697	Approved
0.6733	Remote Similarity	NPD6118	Approved
0.6719	Remote Similarity	NPD7736	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6697	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD8377	Approved
0.6694	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.664	Remote Similarity	NPD8379	Approved
0.664	Remote Similarity	NPD8380	Approved
0.664	Remote Similarity	NPD6921	Approved
0.664	Remote Similarity	NPD8378	Approved
0.664	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD8335	Approved
0.664	Remote Similarity	NPD8296	Approved
0.6639	Remote Similarity	NPD6883	Approved
0.6639	Remote Similarity	NPD7102	Approved
0.6639	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6636	Remote Similarity	NPD4202	Approved
0.6614	Remote Similarity	NPD7492	Approved
0.661	Remote Similarity	NPD6011	Approved
0.6609	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5222	Approved
0.6607	Remote Similarity	NPD5221	Approved
0.6602	Remote Similarity	NPD7525	Registered
0.6585	Remote Similarity	NPD6009	Approved
0.6583	Remote Similarity	NPD6617	Approved
0.6583	Remote Similarity	NPD6847	Approved
0.6583	Remote Similarity	NPD8130	Phase 1
0.6583	Remote Similarity	NPD6869	Approved
0.6583	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD6672	Approved
0.6574	Remote Similarity	NPD6903	Approved
0.6574	Remote Similarity	NPD5737	Approved
0.6562	Remote Similarity	NPD6616	Approved
0.656	Remote Similarity	NPD6059	Approved
0.656	Remote Similarity	NPD6054	Approved
0.6555	Remote Similarity	NPD6013	Approved
0.6555	Remote Similarity	NPD6012	Approved
0.6555	Remote Similarity	NPD6014	Approved
0.6549	Remote Similarity	NPD5173	Approved
0.6549	Remote Similarity	NPD4755	Approved
0.6535	Remote Similarity	NPD6117	Approved
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8293	Discontinued
0.6512	Remote Similarity	NPD7078	Approved
0.6509	Remote Similarity	NPD3668	Phase 3
0.6508	Remote Similarity	NPD7503	Approved
0.6496	Remote Similarity	NPD5141	Approved
0.6491	Remote Similarity	NPD5696	Approved
0.6476	Remote Similarity	NPD4270	Approved
0.6476	Remote Similarity	NPD4269	Approved
0.6476	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6116	Phase 1
0.646	Remote Similarity	NPD7614	Phase 1
0.6457	Remote Similarity	NPD6370	Approved
0.6455	Remote Similarity	NPD5785	Approved
0.6455	Remote Similarity	NPD46	Approved
0.6455	Remote Similarity	NPD6698	Approved
0.6449	Remote Similarity	NPD1694	Approved
0.6446	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5286	Approved
0.6435	Remote Similarity	NPD4700	Approved
0.6435	Remote Similarity	NPD4696	Approved
0.6435	Remote Similarity	NPD5285	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7604	Phase 2
0.6389	Remote Similarity	NPD4623	Approved
0.6389	Remote Similarity	NPD4519	Discontinued
0.6389	Remote Similarity	NPD5786	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6379	Remote Similarity	NPD5344	Discontinued
0.6379	Remote Similarity	NPD5223	Approved
0.6378	Remote Similarity	NPD6015	Approved
0.6378	Remote Similarity	NPD6016	Approved
0.6378	Remote Similarity	NPD5983	Phase 2
0.6372	Remote Similarity	NPD5695	Phase 3
0.6371	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD6371	Approved
0.6337	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7524	Approved
0.633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5988	Approved
0.6325	Remote Similarity	NPD5224	Approved
0.6325	Remote Similarity	NPD4633	Approved
0.6325	Remote Similarity	NPD5226	Approved
0.6325	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD7839	Suspended
0.6316	Remote Similarity	NPD7732	Phase 3
0.6308	Remote Similarity	NPD6336	Discontinued
0.6303	Remote Similarity	NPD4768	Approved
0.6303	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD5363	Approved
0.6286	Remote Similarity	NPD4695	Discontinued
0.6286	Remote Similarity	NPD4252	Approved
0.6275	Remote Similarity	NPD7339	Approved
0.6275	Remote Similarity	NPD6942	Approved
0.6271	Remote Similarity	NPD4754	Approved
0.6271	Remote Similarity	NPD5174	Approved
0.6271	Remote Similarity	NPD5175	Approved
0.627	Remote Similarity	NPD6335	Approved
0.6262	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD5281	Approved
0.624	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD6098	Approved
0.6239	Remote Similarity	NPD5279	Phase 3
0.6228	Remote Similarity	NPD4629	Approved
0.6228	Remote Similarity	NPD5210	Approved
0.6226	Remote Similarity	NPD5369	Approved
0.622	Remote Similarity	NPD7101	Approved
0.622	Remote Similarity	NPD7100	Approved
0.6216	Remote Similarity	NPD6673	Approved
0.6216	Remote Similarity	NPD6051	Approved
0.6216	Remote Similarity	NPD6904	Approved
0.6216	Remote Similarity	NPD6080	Approved
0.6214	Remote Similarity	NPD3701	Clinical (unspecified phase)

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