NPASS Compound

Structure

CID200752 OpenBabel06191715592D 36 40 0 0 1 0 0 0 0 0999 V2000 -4.4770 -0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9985 1.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 -0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 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 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3796 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -2.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 17 32 1 0 0 0 0 18 32 1 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 25 1 1 0 0 0 21 28 1 0 0 0 0 22 32 1 6 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 29 5 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 32 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	7.461
LogD:	5.367
LogS:	-5.788
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	4.715
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.307
MDCK Permeability:	1.5162235285970382e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.522
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	89.1229476928711%
Volume Distribution (VD):	0.669
Pgp-substrate:	6.489347457885742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.247
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.438
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	4.142
Half-life (T1/2):	0.016

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.45
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.278
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.05
Carcinogencity:	0.344
Eye Corrosion:	0.275
Eye Irritation:	0.076
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC200752

Natural Product ID:	NPC200752
*Common Name:**	3 Beta-O-Acetyloleanolic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aS,10S,12aS,14bS)-10-methoxycarbonyl-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	3 Beta-O-Acetyloleanolic Acid
Standard InCHIKey:	HDWYAPCZHCDUNP-JVZQWSIASA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-27(2)15-17-32(26(34)35)18-16-30(6)20(22(32)19-27)9-10-24-29(5)13-11-21(25(33)36-8)28(3,4)23(29)12-14-31(24,30)7/h9,21-24H,10-19H2,1-8H3,(H,34,35)/t21-,22+,23+,24-,29+,30-,31-,32+/m1/s1
SMILES:	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(=O)OC)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503071
PubChem CID:	44583799
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
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792405]
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	1.0	nM	PMID[500818]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	2200.0	nM	PMID[500818]

☑ 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 NPC200752 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	197
0.1-0.2	1310
0.2-0.3	5808
0.3-0.4	16325
0.4-0.5	7425
0.5-0.6	5559
0.6-0.7	4500
0.7-0.8	1168
0.8-0.85	187
0.85-0.9	181
0.9-0.95	35
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.961	High Similarity	NPC477057
0.961	High Similarity	NPC104545
0.9481	High Similarity	NPC16394
0.9351	High Similarity	NPC280654
0.9351	High Similarity	NPC110094
0.9351	High Similarity	NPC260385
0.9241	High Similarity	NPC274050
0.9241	High Similarity	NPC162632
0.9241	High Similarity	NPC263272
0.9241	High Similarity	NPC267691
0.9231	High Similarity	NPC199595
0.9221	High Similarity	NPC471899
0.9221	High Similarity	NPC107039
0.9221	High Similarity	NPC471897
0.9167	High Similarity	NPC120840
0.9167	High Similarity	NPC113989
0.9136	High Similarity	NPC96095
0.9125	High Similarity	NPC251779
0.9125	High Similarity	NPC69101
0.9114	High Similarity	NPC37038
0.9114	High Similarity	NPC267517
0.9091	High Similarity	NPC89294
0.9059	High Similarity	NPC285184
0.9059	High Similarity	NPC77099
0.9059	High Similarity	NPC470590
0.9059	High Similarity	NPC60755
0.9048	High Similarity	NPC30522
0.9048	High Similarity	NPC474700
0.9036	High Similarity	NPC158141
0.9036	High Similarity	NPC173089
0.9012	High Similarity	NPC70834
0.9	High Similarity	NPC221647
0.8987	High Similarity	NPC327674
0.8987	High Similarity	NPC231431
0.8953	High Similarity	NPC169343
0.8953	High Similarity	NPC86368
0.8941	High Similarity	NPC198818
0.8941	High Similarity	NPC474728
0.8929	High Similarity	NPC182797
0.8929	High Similarity	NPC40552
0.8929	High Similarity	NPC52169
0.8929	High Similarity	NPC474474
0.8929	High Similarity	NPC1753
0.8929	High Similarity	NPC474511
0.8929	High Similarity	NPC246708
0.8916	High Similarity	NPC324063
0.8902	High Similarity	NPC156981
0.8902	High Similarity	NPC312660
0.8861	High Similarity	NPC321514
0.8851	High Similarity	NPC78580
0.8851	High Similarity	NPC74751
0.8851	High Similarity	NPC23621
0.8851	High Similarity	NPC296164
0.8851	High Similarity	NPC184006
0.8824	High Similarity	NPC270768
0.8824	High Similarity	NPC198664
0.8824	High Similarity	NPC274330
0.8824	High Similarity	NPC121798
0.8824	High Similarity	NPC281524
0.8824	High Similarity	NPC263393
0.8824	High Similarity	NPC293048
0.8824	High Similarity	NPC127689
0.8824	High Similarity	NPC130520
0.8824	High Similarity	NPC290972
0.8824	High Similarity	NPC470588
0.8824	High Similarity	NPC61543
0.8824	High Similarity	NPC25906
0.8824	High Similarity	NPC59263
0.8824	High Similarity	NPC234346
0.8824	High Similarity	NPC64872
0.8824	High Similarity	NPC143232
0.8824	High Similarity	NPC225585
0.881	High Similarity	NPC130577
0.881	High Similarity	NPC68160
0.881	High Similarity	NPC162107
0.881	High Similarity	NPC51700
0.881	High Similarity	NPC142415
0.881	High Similarity	NPC18064
0.881	High Similarity	NPC46912
0.881	High Similarity	NPC88716
0.881	High Similarity	NPC102683
0.881	High Similarity	NPC98442
0.881	High Similarity	NPC293564
0.881	High Similarity	NPC242468
0.881	High Similarity	NPC171203
0.881	High Similarity	NPC307426
0.8765	High Similarity	NPC142244
0.8765	High Similarity	NPC327002
0.8765	High Similarity	NPC3915
0.8765	High Similarity	NPC471898
0.875	High Similarity	NPC474727
0.875	High Similarity	NPC23241
0.875	High Similarity	NPC195715
0.8736	High Similarity	NPC272075
0.8736	High Similarity	NPC307335
0.8736	High Similarity	NPC295643
0.8736	High Similarity	NPC136313
0.8736	High Similarity	NPC74855
0.8736	High Similarity	NPC214756
0.8721	High Similarity	NPC290614
0.8721	High Similarity	NPC291028
0.8721	High Similarity	NPC227467
0.8721	High Similarity	NPC46441
0.8721	High Similarity	NPC126369
0.8721	High Similarity	NPC193750
0.8721	High Similarity	NPC130278
0.8721	High Similarity	NPC210037
0.8721	High Similarity	NPC120968
0.8721	High Similarity	NPC273621
0.8721	High Similarity	NPC18872
0.8721	High Similarity	NPC477872
0.8721	High Similarity	NPC111110
0.8721	High Similarity	NPC7260
0.8721	High Similarity	NPC470589
0.8718	High Similarity	NPC279666
0.8718	High Similarity	NPC192540
0.8706	High Similarity	NPC470629
0.8706	High Similarity	NPC290690
0.8706	High Similarity	NPC17733
0.8706	High Similarity	NPC473242
0.8706	High Similarity	NPC181225
0.8706	High Similarity	NPC474512
0.8701	High Similarity	NPC36310
0.869	High Similarity	NPC72638
0.869	High Similarity	NPC10005
0.869	High Similarity	NPC9892
0.869	High Similarity	NPC329943
0.869	High Similarity	NPC91525
0.8659	High Similarity	NPC310989
0.8652	High Similarity	NPC230151
0.8652	High Similarity	NPC327179
0.8636	High Similarity	NPC91010
0.8621	High Similarity	NPC65120
0.8621	High Similarity	NPC38754
0.8621	High Similarity	NPC288833
0.8621	High Similarity	NPC228784
0.8621	High Similarity	NPC187722
0.8621	High Similarity	NPC235884
0.8621	High Similarity	NPC155120
0.8621	High Similarity	NPC474525
0.8621	High Similarity	NPC158030
0.8621	High Similarity	NPC472149
0.8621	High Similarity	NPC324341
0.8621	High Similarity	NPC282616
0.8621	High Similarity	NPC4036
0.8621	High Similarity	NPC6255
0.8621	High Similarity	NPC105189
0.8621	High Similarity	NPC966
0.8621	High Similarity	NPC233455
0.8621	High Similarity	NPC300351
0.8621	High Similarity	NPC52021
0.8621	High Similarity	NPC145067
0.8621	High Similarity	NPC25299
0.8621	High Similarity	NPC471588
0.8621	High Similarity	NPC306541
0.8621	High Similarity	NPC84319
0.8621	High Similarity	NPC71074
0.8608	High Similarity	NPC69143
0.8605	High Similarity	NPC161751
0.8605	High Similarity	NPC475049
0.8605	High Similarity	NPC474972
0.8605	High Similarity	NPC95246
0.859	High Similarity	NPC103958
0.859	High Similarity	NPC166797
0.859	High Similarity	NPC161923
0.859	High Similarity	NPC241854
0.859	High Similarity	NPC183503
0.859	High Similarity	NPC251970
0.859	High Similarity	NPC283908
0.859	High Similarity	NPC476046
0.859	High Similarity	NPC255168
0.8588	High Similarity	NPC71507
0.8571	High Similarity	NPC160817
0.8571	High Similarity	NPC474537
0.8556	High Similarity	NPC476878
0.8556	High Similarity	NPC158347
0.8556	High Similarity	NPC26413
0.8556	High Similarity	NPC476879
0.8537	High Similarity	NPC278459
0.8523	High Similarity	NPC118519
0.8523	High Similarity	NPC118490
0.8523	High Similarity	NPC158059
0.8523	High Similarity	NPC275809
0.8523	High Similarity	NPC229281
0.8523	High Similarity	NPC263780
0.8523	High Similarity	NPC49776
0.8523	High Similarity	NPC474436
0.8523	High Similarity	NPC298554
0.8523	High Similarity	NPC63118
0.8523	High Similarity	NPC202728
0.8506	High Similarity	NPC49320
0.8506	High Similarity	NPC86372
0.8506	High Similarity	NPC172361
0.8488	Intermediate Similarity	NPC224145
0.8471	Intermediate Similarity	NPC325594
0.8471	Intermediate Similarity	NPC73038
0.8462	Intermediate Similarity	NPC471966
0.8462	Intermediate Similarity	NPC260149
0.8462	Intermediate Similarity	NPC58942
0.8452	Intermediate Similarity	NPC477289

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 NPC200752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1673
0.2-0.3	4050
0.3-0.4	2214
0.4-0.5	595
0.5-0.6	232
0.6-0.7	178
0.7-0.8	27
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8851	High Similarity	NPD7748	Approved
0.8621	High Similarity	NPD7515	Phase 2
0.8556	High Similarity	NPD7902	Approved
0.8222	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD7900	Approved
0.8182	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6399	Phase 3
0.7865	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD8034	Phase 2
0.7802	Intermediate Similarity	NPD8035	Phase 2
0.7727	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD5737	Approved
0.766	Intermediate Similarity	NPD7614	Phase 1
0.766	Intermediate Similarity	NPD7732	Phase 3
0.7647	Intermediate Similarity	NPD7645	Phase 2
0.764	Intermediate Similarity	NPD7334	Approved
0.764	Intermediate Similarity	NPD6409	Approved
0.764	Intermediate Similarity	NPD5330	Approved
0.764	Intermediate Similarity	NPD7146	Approved
0.764	Intermediate Similarity	NPD6684	Approved
0.764	Intermediate Similarity	NPD7521	Approved
0.7614	Intermediate Similarity	NPD4786	Approved
0.7586	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD6083	Phase 2
0.7558	Intermediate Similarity	NPD4695	Discontinued
0.7473	Intermediate Similarity	NPD6903	Approved
0.7444	Intermediate Similarity	NPD6098	Approved
0.7416	Intermediate Similarity	NPD3665	Phase 1
0.7416	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD6673	Approved
0.7391	Intermediate Similarity	NPD6904	Approved
0.7391	Intermediate Similarity	NPD6080	Approved
0.7386	Intermediate Similarity	NPD4221	Approved
0.7386	Intermediate Similarity	NPD4223	Phase 3
0.7386	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7363	Intermediate Similarity	NPD3573	Approved
0.7333	Intermediate Similarity	NPD5329	Approved
0.732	Intermediate Similarity	NPD5696	Approved
0.7253	Intermediate Similarity	NPD3618	Phase 1
0.7234	Intermediate Similarity	NPD5284	Approved
0.7234	Intermediate Similarity	NPD5281	Approved
0.7234	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD4197	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7204	Intermediate Similarity	NPD4753	Phase 2
0.7204	Intermediate Similarity	NPD5328	Approved
0.7188	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7638	Approved
0.7126	Intermediate Similarity	NPD3617	Approved
0.7097	Intermediate Similarity	NPD5208	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7065	Intermediate Similarity	NPD4623	Approved
0.7065	Intermediate Similarity	NPD4693	Phase 3
0.7065	Intermediate Similarity	NPD4690	Approved
0.7065	Intermediate Similarity	NPD4519	Discontinued
0.7065	Intermediate Similarity	NPD5205	Approved
0.7065	Intermediate Similarity	NPD4138	Approved
0.7065	Intermediate Similarity	NPD4689	Approved
0.7065	Intermediate Similarity	NPD4688	Approved
0.7065	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7053	Intermediate Similarity	NPD5693	Phase 1
0.7053	Intermediate Similarity	NPD6079	Approved
0.7053	Intermediate Similarity	NPD6050	Approved
0.7021	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6101	Approved
0.6977	Remote Similarity	NPD8039	Approved
0.6947	Remote Similarity	NPD5692	Phase 3
0.6923	Remote Similarity	NPD4788	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6887	Remote Similarity	NPD8130	Phase 1
0.6882	Remote Similarity	NPD4694	Approved
0.6882	Remote Similarity	NPD5280	Approved
0.6882	Remote Similarity	NPD5690	Phase 2
0.6882	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD5694	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6857	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4629	Approved
0.6837	Remote Similarity	NPD5210	Approved
0.6829	Remote Similarity	NPD4224	Phase 2
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6827	Remote Similarity	NPD6412	Phase 2
0.6824	Remote Similarity	NPD6081	Approved
0.6824	Remote Similarity	NPD4243	Approved
0.6822	Remote Similarity	NPD8297	Approved
0.6814	Remote Similarity	NPD8328	Phase 3
0.6804	Remote Similarity	NPD4202	Approved
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD4137	Phase 3
0.6782	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD6942	Approved
0.6778	Remote Similarity	NPD7525	Registered
0.6771	Remote Similarity	NPD5207	Approved
0.6768	Remote Similarity	NPD4697	Phase 3
0.6768	Remote Similarity	NPD5221	Approved
0.6768	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5222	Approved
0.6762	Remote Similarity	NPD6011	Approved
0.6735	Remote Similarity	NPD6001	Approved
0.6733	Remote Similarity	NPD6404	Discontinued
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD6650	Approved
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4747	Approved
0.6706	Remote Similarity	NPD4691	Approved
0.6705	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6117	Approved
0.6703	Remote Similarity	NPD8028	Phase 2
0.6703	Remote Similarity	NPD4139	Approved
0.6703	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD4755	Approved
0.67	Remote Similarity	NPD5173	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.6633	Remote Similarity	NPD5778	Approved
0.6629	Remote Similarity	NPD6116	Phase 1
0.6604	Remote Similarity	NPD6686	Approved
0.6577	Remote Similarity	NPD7115	Discovery
0.6569	Remote Similarity	NPD5285	Approved
0.6569	Remote Similarity	NPD5286	Approved
0.6569	Remote Similarity	NPD4700	Approved
0.6569	Remote Similarity	NPD4696	Approved
0.6556	Remote Similarity	NPD6115	Approved
0.6556	Remote Similarity	NPD6697	Approved
0.6556	Remote Similarity	NPD6118	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6114	Approved
0.6538	Remote Similarity	NPD6052	Approved
0.6505	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD5654	Approved
0.6486	Remote Similarity	NPD6868	Approved
0.6477	Remote Similarity	NPD5733	Approved
0.6477	Remote Similarity	NPD4058	Approved
0.6455	Remote Similarity	NPD8133	Approved
0.6455	Remote Similarity	NPD4632	Approved
0.6442	Remote Similarity	NPD5225	Approved
0.6442	Remote Similarity	NPD5224	Approved
0.6442	Remote Similarity	NPD4633	Approved
0.6442	Remote Similarity	NPD5211	Phase 2
0.6442	Remote Similarity	NPD5226	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6437	Remote Similarity	NPD5777	Approved
0.6429	Remote Similarity	NPD7331	Phase 2
0.6429	Remote Similarity	NPD4096	Approved
0.6421	Remote Similarity	NPD1694	Approved
0.6415	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD5275	Approved
0.6404	Remote Similarity	NPD3702	Approved
0.6404	Remote Similarity	NPD4190	Phase 3
0.6383	Remote Similarity	NPD5362	Discontinued
0.6381	Remote Similarity	NPD5174	Approved
0.6381	Remote Similarity	NPD4754	Approved
0.6381	Remote Similarity	NPD5175	Approved
0.6373	Remote Similarity	NPD5959	Approved
0.6372	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6355	Remote Similarity	NPD6614	Approved
0.6344	Remote Similarity	NPD5369	Approved
0.6339	Remote Similarity	NPD6274	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.6322	Remote Similarity	NPD4245	Approved
0.6322	Remote Similarity	NPD4244	Approved
0.6321	Remote Similarity	NPD5141	Approved
0.6316	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD7100	Approved
0.6311	Remote Similarity	NPD4225	Approved
0.631	Remote Similarity	NPD7341	Phase 2
0.6306	Remote Similarity	NPD6858	Approved
0.6306	Remote Similarity	NPD7094	Approved
0.6303	Remote Similarity	NPD7736	Approved
0.63	Remote Similarity	NPD5133	Approved
0.6292	Remote Similarity	NPD4687	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