NPASS Compound

Structure

NPC88847 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 5.0662 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0206 0.6181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3775 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 2.9250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 2.4375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5331 1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 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 2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9956 0.6181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 3.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 16 31 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 23 2 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 20 32 1 6 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 1 0 0 0 24 33 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	4.083
LogD:	3.251
LogS:	-3.843
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	5.181
Fsp3:	0.833
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:	-5.363
MDCK Permeability:	1.237666674569482e-05
Pgp-inhibitor:	0.31
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	93.69538116455078%
Volume Distribution (VD):	0.616
Pgp-substrate:	2.4518449306488037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.152
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.473
CYP3A4-substrate:	0.736

ADMET: Excretion

Clearance (CL):	1.352
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.568
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.743
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.218
Carcinogencity:	0.03
Eye Corrosion:	0.01
Eye Irritation:	0.032
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC88847

Natural Product ID:	NPC88847
*Common Name:**	2Alpha,3Beta,23-Trihydroxyurs-12,18-Dien-28-Oic Acid
IUPAC Name:	(2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13-dodecahydro-2H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	VGQCVDQJFOPLQF-VENSNSCWSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17,20-22,24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,20-,21-,22-,24+,26+,27+,28-,29-,30+/m1/s1
SMILES:	OC[C@]1(C)[C@@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1(C2=C(C)[C@@H](CC1)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516291
PubChem CID:	15275863
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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
Others	6

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	51.5	%	PMID[519205]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	30.8	%	PMID[519205]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	29.4	%	PMID[519205]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	149.9	%	PMID[519205]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	47.4	%	PMID[519205]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	40.6	%	PMID[519205]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	51000.0	nM	PMID[519205]

☑ 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 NPC88847 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	221
0.1-0.2	1183
0.2-0.3	4328
0.3-0.4	10859
0.4-0.5	12389
0.5-0.6	5921
0.6-0.7	5569
0.7-0.8	1866
0.8-0.85	179
0.85-0.9	157
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC32118
0.9444	High Similarity	NPC133579
0.9444	High Similarity	NPC474806
0.9348	High Similarity	NPC173744
0.9348	High Similarity	NPC204961
0.9348	High Similarity	NPC73004
0.9341	High Similarity	NPC32407
0.9341	High Similarity	NPC231063
0.9341	High Similarity	NPC263548
0.9341	High Similarity	NPC282395
0.9341	High Similarity	NPC299996
0.9341	High Similarity	NPC145667
0.9341	High Similarity	NPC80365
0.9341	High Similarity	NPC20235
0.9341	High Similarity	NPC88116
0.9247	High Similarity	NPC9613
0.9247	High Similarity	NPC247139
0.9239	High Similarity	NPC96916
0.9222	High Similarity	NPC49320
0.9149	High Similarity	NPC29765
0.9149	High Similarity	NPC271614
0.9149	High Similarity	NPC111214
0.914	High Similarity	NPC25848
0.914	High Similarity	NPC259733
0.914	High Similarity	NPC207922
0.914	High Similarity	NPC305464
0.914	High Similarity	NPC158371
0.914	High Similarity	NPC307282
0.914	High Similarity	NPC19376
0.914	High Similarity	NPC201657
0.9121	High Similarity	NPC472149
0.9121	High Similarity	NPC25299
0.9121	High Similarity	NPC301244
0.9121	High Similarity	NPC52021
0.9121	High Similarity	NPC84319
0.9121	High Similarity	NPC306541
0.9121	High Similarity	NPC235884
0.9121	High Similarity	NPC71074
0.9121	High Similarity	NPC300351
0.9053	High Similarity	NPC35239
0.9043	High Similarity	NPC255589
0.9043	High Similarity	NPC43686
0.9043	High Similarity	NPC259788
0.9043	High Similarity	NPC106112
0.9043	High Similarity	NPC261935
0.9022	High Similarity	NPC136313
0.9022	High Similarity	NPC275809
0.9022	High Similarity	NPC229281
0.9022	High Similarity	NPC74855
0.9022	High Similarity	NPC307335
0.9011	High Similarity	NPC130278
0.9011	High Similarity	NPC470589
0.9011	High Similarity	NPC126369
0.9011	High Similarity	NPC111110
0.8958	High Similarity	NPC256247
0.8925	High Similarity	NPC191412
0.8925	High Similarity	NPC114159
0.8925	High Similarity	NPC87095
0.8925	High Similarity	NPC6818
0.8913	High Similarity	NPC187722
0.8913	High Similarity	NPC235704
0.8901	High Similarity	NPC225585
0.8901	High Similarity	NPC293048
0.8901	High Similarity	NPC130520
0.8901	High Similarity	NPC25906
0.8901	High Similarity	NPC64872
0.8901	High Similarity	NPC95246
0.8901	High Similarity	NPC274330
0.8901	High Similarity	NPC474972
0.8901	High Similarity	NPC474686
0.8901	High Similarity	NPC234346
0.8901	High Similarity	NPC161751
0.8901	High Similarity	NPC127689
0.8901	High Similarity	NPC290972
0.8901	High Similarity	NPC263393
0.8901	High Similarity	NPC61543
0.8901	High Similarity	NPC198664
0.8901	High Similarity	NPC59263
0.8901	High Similarity	NPC270768
0.8901	High Similarity	NPC121798
0.8901	High Similarity	NPC143232
0.8889	High Similarity	NPC71507
0.8842	High Similarity	NPC21728
0.883	High Similarity	NPC198245
0.8817	High Similarity	NPC158059
0.8817	High Similarity	NPC118519
0.8817	High Similarity	NPC202728
0.8804	High Similarity	NPC273621
0.8804	High Similarity	NPC18872
0.8804	High Similarity	NPC210037
0.8804	High Similarity	NPC227467
0.8804	High Similarity	NPC477872
0.8804	High Similarity	NPC7260
0.8804	High Similarity	NPC290614
0.8804	High Similarity	NPC120968
0.8791	High Similarity	NPC181225
0.8791	High Similarity	NPC474512
0.8791	High Similarity	NPC17733
0.8791	High Similarity	NPC473242
0.8791	High Similarity	NPC470629
0.8791	High Similarity	NPC290690
0.8791	High Similarity	NPC182797
0.8791	High Similarity	NPC52169
0.8778	High Similarity	NPC56588
0.8778	High Similarity	NPC72638
0.8764	High Similarity	NPC171789
0.8763	High Similarity	NPC54909
0.8763	High Similarity	NPC233012
0.8737	High Similarity	NPC116457
0.8737	High Similarity	NPC473158
0.8737	High Similarity	NPC132824
0.8737	High Similarity	NPC9487
0.8737	High Similarity	NPC230151
0.8737	High Similarity	NPC476318
0.8737	High Similarity	NPC476327
0.8723	High Similarity	NPC188102
0.8723	High Similarity	NPC159365
0.871	High Similarity	NPC324341
0.871	High Similarity	NPC105189
0.871	High Similarity	NPC282616
0.871	High Similarity	NPC966
0.871	High Similarity	NPC475708
0.871	High Similarity	NPC228784
0.871	High Similarity	NPC288833
0.871	High Similarity	NPC38754
0.871	High Similarity	NPC155120
0.8696	High Similarity	NPC470588
0.8681	High Similarity	NPC477926
0.8681	High Similarity	NPC242468
0.8681	High Similarity	NPC293564
0.8681	High Similarity	NPC307426
0.8681	High Similarity	NPC102683
0.8681	High Similarity	NPC18064
0.8681	High Similarity	NPC98442
0.8681	High Similarity	NPC51700
0.8681	High Similarity	NPC68160
0.8681	High Similarity	NPC88716
0.8681	High Similarity	NPC130577
0.8681	High Similarity	NPC171203
0.8681	High Similarity	NPC142415
0.8646	High Similarity	NPC312075
0.8646	High Similarity	NPC203343
0.8641	High Similarity	NPC212968
0.8641	High Similarity	NPC125923
0.8641	High Similarity	NPC65590
0.8641	High Similarity	NPC64106
0.8632	High Similarity	NPC53565
0.8632	High Similarity	NPC473240
0.8617	High Similarity	NPC86368
0.8617	High Similarity	NPC118490
0.8602	High Similarity	NPC193750
0.8602	High Similarity	NPC291028
0.8602	High Similarity	NPC86372
0.8602	High Similarity	NPC474728
0.8602	High Similarity	NPC172361
0.8587	High Similarity	NPC246708
0.8587	High Similarity	NPC40552
0.8557	High Similarity	NPC174663
0.8557	High Similarity	NPC188833
0.8544	High Similarity	NPC190837
0.8542	High Similarity	NPC62516
0.8542	High Similarity	NPC157113
0.8542	High Similarity	NPC327179
0.8526	High Similarity	NPC209868
0.8526	High Similarity	NPC222047
0.8526	High Similarity	NPC296164
0.8511	High Similarity	NPC474525
0.8511	High Similarity	NPC60755
0.8511	High Similarity	NPC4036
0.8511	High Similarity	NPC6255
0.8511	High Similarity	NPC285184
0.8511	High Similarity	NPC233455
0.8511	High Similarity	NPC471588
0.8511	High Similarity	NPC189520
0.8511	High Similarity	NPC470590
0.8511	High Similarity	NPC65120
0.8511	High Similarity	NPC473167
0.8511	High Similarity	NPC158030
0.8511	High Similarity	NPC77099
0.8511	High Similarity	NPC145067
0.85	High Similarity	NPC475036
0.85	High Similarity	NPC284865
0.8495	Intermediate Similarity	NPC30522
0.8469	Intermediate Similarity	NPC476195
0.8462	Intermediate Similarity	NPC161434
0.8462	Intermediate Similarity	NPC195132
0.8454	Intermediate Similarity	NPC187933
0.8454	Intermediate Similarity	NPC189880
0.8438	Intermediate Similarity	NPC195715
0.8438	Intermediate Similarity	NPC148523
0.8438	Intermediate Similarity	NPC139570
0.8438	Intermediate Similarity	NPC83693
0.8421	Intermediate Similarity	NPC211230
0.8421	Intermediate Similarity	NPC298554
0.8421	Intermediate Similarity	NPC214756
0.8421	Intermediate Similarity	NPC295643
0.8421	Intermediate Similarity	NPC272075
0.8416	Intermediate Similarity	NPC477877
0.8404	Intermediate Similarity	NPC113989
0.8404	Intermediate Similarity	NPC46441

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 NPC88847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1500
0.2-0.3	3659
0.3-0.4	2487
0.4-0.5	838
0.5-0.6	217
0.6-0.7	217
0.7-0.8	32
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD7515	Phase 2
0.8144	Intermediate Similarity	NPD7748	Approved
0.8105	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7902	Approved
0.783	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7900	Approved
0.7755	Intermediate Similarity	NPD6411	Approved
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6399	Phase 3
0.7609	Intermediate Similarity	NPD7645	Phase 2
0.7579	Intermediate Similarity	NPD4786	Approved
0.7553	Intermediate Similarity	NPD3667	Approved
0.7551	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6101	Approved
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.7383	Intermediate Similarity	NPD7128	Approved
0.7383	Intermediate Similarity	NPD6675	Approved
0.7383	Intermediate Similarity	NPD5739	Approved
0.7383	Intermediate Similarity	NPD6402	Approved
0.7374	Intermediate Similarity	NPD5328	Approved
0.7345	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6899	Approved
0.7248	Intermediate Similarity	NPD6881	Approved
0.7228	Intermediate Similarity	NPD6079	Approved
0.7212	Intermediate Similarity	NPD4755	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6373	Approved
0.7158	Intermediate Similarity	NPD7525	Registered
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD4202	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7156	Intermediate Similarity	NPD5701	Approved
0.7156	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7119	Intermediate Similarity	NPD8328	Phase 3
0.7117	Intermediate Similarity	NPD7290	Approved
0.7117	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7102	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6117	Approved
0.7075	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7075	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD5279	Phase 3
0.7059	Intermediate Similarity	NPD5284	Approved
0.7059	Intermediate Similarity	NPD5281	Approved
0.7054	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6083	Phase 2
0.7048	Intermediate Similarity	NPD6084	Phase 2
0.7041	Intermediate Similarity	NPD3133	Approved
0.7041	Intermediate Similarity	NPD3666	Approved
0.7041	Intermediate Similarity	NPD3665	Phase 1
0.7041	Intermediate Similarity	NPD3668	Phase 3
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.6991	Remote Similarity	NPD6882	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD5221	Approved
0.6952	Remote Similarity	NPD4697	Phase 3
0.6952	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD5224	Approved
0.6937	Remote Similarity	NPD6011	Approved
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4632	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7334	Approved
0.69	Remote Similarity	NPD6409	Approved
0.69	Remote Similarity	NPD6684	Approved
0.69	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD7146	Approved
0.69	Remote Similarity	NPD7521	Approved
0.6887	Remote Similarity	NPD5173	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6863	Remote Similarity	NPD4753	Phase 2
0.6857	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD5223	Approved
0.6832	Remote Similarity	NPD3573	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD4634	Approved
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD6942	Approved
0.6804	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4695	Discontinued
0.6792	Remote Similarity	NPD7732	Phase 3
0.6786	Remote Similarity	NPD6686	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6765	Remote Similarity	NPD6672	Approved
0.6765	Remote Similarity	NPD6903	Approved
0.6765	Remote Similarity	NPD5737	Approved
0.6757	Remote Similarity	NPD4768	Approved
0.6757	Remote Similarity	NPD4767	Approved
0.6737	Remote Similarity	NPD6933	Approved
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4754	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6721	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6632	Remote Similarity	NPD8264	Approved
0.6613	Remote Similarity	NPD7736	Approved
0.661	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD6050	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD5280	Approved
0.6569	Remote Similarity	NPD4694	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6555	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4629	Approved
0.6542	Remote Similarity	NPD5210	Approved
0.6542	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD7503	Approved
0.6529	Remote Similarity	NPD8513	Phase 3
0.6529	Remote Similarity	NPD8517	Approved
0.6529	Remote Similarity	NPD8515	Approved
0.6529	Remote Similarity	NPD8516	Approved
0.6529	Remote Similarity	NPD8033	Approved
0.6529	Remote Similarity	NPD6908	Approved
0.6526	Remote Similarity	NPD6924	Approved
0.6526	Remote Similarity	NPD6926	Approved
0.6525	Remote Similarity	NPD6868	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6505	Remote Similarity	NPD7524	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD4221	Approved
0.65	Remote Similarity	NPD4223	Phase 3
0.65	Remote Similarity	NPD7516	Approved
0.6489	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5692	Phase 3
0.6471	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD5329	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6465	Remote Similarity	NPD7509	Discontinued
0.6452	Remote Similarity	NPD6616	Approved
0.6452	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8377	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6446	Remote Similarity	NPD8294	Approved
0.6446	Remote Similarity	NPD6059	Approved
0.6436	Remote Similarity	NPD4788	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6423	Remote Similarity	NPD7604	Phase 2
0.6417	Remote Similarity	NPD7327	Approved
0.6417	Remote Similarity	NPD6314	Approved
0.6417	Remote Similarity	NPD7328	Approved
0.6417	Remote Similarity	NPD6313	Approved
0.6415	Remote Similarity	NPD5694	Approved
0.6415	Remote Similarity	NPD7983	Approved
0.6408	Remote Similarity	NPD6098	Approved
0.64	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD7078	Approved
0.6393	Remote Similarity	NPD8335	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