NPASS Compound

Structure

NPC260149 OpenBabel07101718242D 37 41 0 0 1 0 0 0 0 0999 V2000 3.3816 4.8810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3578 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8697 0.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3578 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8697 1.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5362 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3816 2.9286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5362 1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6908 1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 0.4881 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 5.0724 4.8810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 3.4167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 31 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 32 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 0 0 0 0 19 33 2 0 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 0 0 0 0 21 29 1 1 0 0 0 22 25 1 0 0 0 0 22 34 1 6 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 28 1 0 0 0 0 24 37 1 6 0 0 0 25 28 1 0 0 0 0 25 30 1 6 0 0 0 26 35 2 0 0 0 0 26 36 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 31 32 1 1 0 0 0 32 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.37
Volume:	555.287
LogP:	5.951
LogD:	4.785
LogS:	-4.922
# Rotatable Bonds:	3
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	4.978
Fsp3:	0.875
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.289
MDCK Permeability:	4.47080637968611e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.271

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.02649688720703%
Volume Distribution (VD):	0.805
Pgp-substrate:	3.5061795711517334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	1.785
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.298
Skin Sensitization:	0.224
Carcinogencity:	0.012
Eye Corrosion:	0.053
Eye Irritation:	0.43
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC260149

Natural Product ID:	NPC260149
*Common Name:**	3Beta-Acetoxy-6Beta-Hydroxyolean-12-En-27-Oic Acid
IUPAC Name:	(4aR,6aR,6aR,6bR,8R,8aR,10S,12aR,14bR)-10-acetyloxy-8-hydroxy-2,2,4a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	LDDKVXSYAVQNFD-ZCFZIILGSA-N
Standard InCHI:	InChI=1S/C32H50O5/c1-19(33)37-24-11-12-30(7)23-10-9-20-21-17-27(2,3)13-14-29(21,6)15-16-32(20,26(35)36)31(23,8)18-22(34)25(30)28(24,4)5/h9,21-25,34H,10-18H2,1-8H3,(H,35,36)/t21-,22+,23+,24-,25-,29+,30+,31+,32+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)[C@H](O)C[C@@]1([C@@H]2CC=C2[C@]1(CC[C@@]1([C@H]2CC(C)(C)CC1)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560057
PubChem CID:	45267298
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
NPO6947	Astilbe chinensis	Species	Saxifragaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19585998]
NPO6947	Astilbe chinensis	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6947	Astilbe chinensis	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6947	Astilbe chinensis	Species	Saxifragaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[530494]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[530494]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[530494]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5100.0	nM	PMID[530494]
NPT788	Cell Line	SNU1	Homo sapiens	IC50	>	10000.0	nM	PMID[530494]

☑ 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 NPC260149 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	226
0.1-0.2	1407
0.2-0.3	4541
0.3-0.4	10291
0.4-0.5	11818
0.5-0.6	6069
0.6-0.7	4929
0.7-0.8	2561
0.8-0.85	551
0.85-0.9	227
0.9-0.95	72
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC58942
0.967	High Similarity	NPC473240
0.9565	High Similarity	NPC476318
0.9565	High Similarity	NPC476327
0.9462	High Similarity	NPC189880
0.9457	High Similarity	NPC474727
0.9362	High Similarity	NPC475876
0.9355	High Similarity	NPC327179
0.9341	High Similarity	NPC60755
0.9341	High Similarity	NPC470590
0.9341	High Similarity	NPC77099
0.9341	High Similarity	NPC285184
0.9255	High Similarity	NPC476878
0.9255	High Similarity	NPC476879
0.9239	High Similarity	NPC86368
0.9231	High Similarity	NPC120840
0.9231	High Similarity	NPC113989
0.9231	High Similarity	NPC474728
0.914	High Similarity	NPC159365
0.913	High Similarity	NPC187722
0.9121	High Similarity	NPC198664
0.9121	High Similarity	NPC64872
0.9121	High Similarity	NPC274330
0.9121	High Similarity	NPC470588
0.9121	High Similarity	NPC25906
0.9121	High Similarity	NPC143232
0.9121	High Similarity	NPC30522
0.9121	High Similarity	NPC290972
0.9053	High Similarity	NPC43686
0.9043	High Similarity	NPC139570
0.9043	High Similarity	NPC195715
0.9032	High Similarity	NPC118519
0.9032	High Similarity	NPC202728
0.9032	High Similarity	NPC158059
0.9032	High Similarity	NPC229281
0.9022	High Similarity	NPC290614
0.9022	High Similarity	NPC126369
0.9022	High Similarity	NPC477872
0.9022	High Similarity	NPC7260
0.9022	High Similarity	NPC210037
0.9022	High Similarity	NPC111110
0.9022	High Similarity	NPC227467
0.9022	High Similarity	NPC130278
0.9022	High Similarity	NPC273621
0.9022	High Similarity	NPC18872
0.9022	High Similarity	NPC120968
0.9022	High Similarity	NPC470589
0.9011	High Similarity	NPC40552
0.9011	High Similarity	NPC474512
0.9011	High Similarity	NPC17733
0.9011	High Similarity	NPC52169
0.9011	High Similarity	NPC470629
0.9011	High Similarity	NPC290690
0.9011	High Similarity	NPC182797
0.9011	High Similarity	NPC181225
0.9011	High Similarity	NPC473242
0.9011	High Similarity	NPC246708
0.899	High Similarity	NPC231530
0.899	High Similarity	NPC278628
0.8969	High Similarity	NPC233012
0.8969	High Similarity	NPC54909
0.8947	High Similarity	NPC230151
0.8947	High Similarity	NPC19376
0.8947	High Similarity	NPC25848
0.8947	High Similarity	NPC307282
0.8947	High Similarity	NPC305464
0.8936	High Similarity	NPC184006
0.8936	High Similarity	NPC23621
0.8936	High Similarity	NPC474529
0.8936	High Similarity	NPC296164
0.8936	High Similarity	NPC6818
0.8936	High Similarity	NPC191412
0.8936	High Similarity	NPC114159
0.8936	High Similarity	NPC78580
0.8936	High Similarity	NPC74751
0.8925	High Similarity	NPC105189
0.8925	High Similarity	NPC475708
0.8925	High Similarity	NPC38754
0.8913	High Similarity	NPC130520
0.8913	High Similarity	NPC263393
0.8913	High Similarity	NPC61543
0.8913	High Similarity	NPC270768
0.8913	High Similarity	NPC121798
0.8913	High Similarity	NPC225585
0.8913	High Similarity	NPC293048
0.8913	High Similarity	NPC59263
0.8913	High Similarity	NPC234346
0.8913	High Similarity	NPC127689
0.8901	High Similarity	NPC307426
0.8901	High Similarity	NPC293564
0.8901	High Similarity	NPC102683
0.8901	High Similarity	NPC171203
0.8901	High Similarity	NPC142415
0.8901	High Similarity	NPC242468
0.8901	High Similarity	NPC18064
0.8901	High Similarity	NPC162107
0.8901	High Similarity	NPC88716
0.8901	High Similarity	NPC98442
0.8901	High Similarity	NPC68160
0.8901	High Similarity	NPC46912
0.8901	High Similarity	NPC130577
0.8901	High Similarity	NPC51700
0.8866	High Similarity	NPC476195
0.8854	High Similarity	NPC259788
0.8854	High Similarity	NPC255589
0.8854	High Similarity	NPC158347
0.8842	High Similarity	NPC96916
0.8842	High Similarity	NPC23241
0.883	High Similarity	NPC49776
0.883	High Similarity	NPC307335
0.883	High Similarity	NPC63118
0.883	High Similarity	NPC214756
0.883	High Similarity	NPC74855
0.883	High Similarity	NPC295643
0.883	High Similarity	NPC272075
0.883	High Similarity	NPC474436
0.883	High Similarity	NPC136313
0.8817	High Similarity	NPC291028
0.8817	High Similarity	NPC193750
0.8812	High Similarity	NPC94529
0.88	High Similarity	NPC477877
0.8791	High Similarity	NPC9892
0.8791	High Similarity	NPC137306
0.8791	High Similarity	NPC329943
0.8791	High Similarity	NPC84121
0.8791	High Similarity	NPC325594
0.8791	High Similarity	NPC72638
0.8791	High Similarity	NPC10005
0.8791	High Similarity	NPC91525
0.8776	High Similarity	NPC476132
0.8776	High Similarity	NPC118964
0.8776	High Similarity	NPC256247
0.8763	High Similarity	NPC471966
0.8763	High Similarity	NPC164349
0.875	High Similarity	NPC204961
0.875	High Similarity	NPC157113
0.875	High Similarity	NPC73004
0.875	High Similarity	NPC116457
0.875	High Similarity	NPC173744
0.875	High Similarity	NPC132824
0.875	High Similarity	NPC207922
0.875	High Similarity	NPC158371
0.875	High Similarity	NPC62516
0.875	High Similarity	NPC259733
0.8737	High Similarity	NPC474963
0.8737	High Similarity	NPC209868
0.8737	High Similarity	NPC263548
0.8737	High Similarity	NPC88116
0.8737	High Similarity	NPC32407
0.8737	High Similarity	NPC145667
0.8737	High Similarity	NPC91010
0.8737	High Similarity	NPC299996
0.8737	High Similarity	NPC231063
0.8737	High Similarity	NPC20235
0.8737	High Similarity	NPC282395
0.8725	High Similarity	NPC310546
0.8723	High Similarity	NPC145067
0.8723	High Similarity	NPC25299
0.8723	High Similarity	NPC235884
0.8723	High Similarity	NPC233455
0.8723	High Similarity	NPC71074
0.8723	High Similarity	NPC155120
0.8723	High Similarity	NPC282616
0.8723	High Similarity	NPC300351
0.8723	High Similarity	NPC228784
0.8723	High Similarity	NPC52021
0.8723	High Similarity	NPC474525
0.8723	High Similarity	NPC472149
0.8723	High Similarity	NPC324341
0.8723	High Similarity	NPC158030
0.8723	High Similarity	NPC306541
0.8723	High Similarity	NPC966
0.8723	High Similarity	NPC4036
0.8723	High Similarity	NPC288833
0.8723	High Similarity	NPC65120
0.8723	High Similarity	NPC84319
0.871	High Similarity	NPC161751
0.871	High Similarity	NPC474972
0.871	High Similarity	NPC95246
0.871	High Similarity	NPC474686
0.871	High Similarity	NPC475049
0.87	High Similarity	NPC475036
0.8696	High Similarity	NPC71507
0.8681	High Similarity	NPC191965
0.8673	High Similarity	NPC473576
0.8673	High Similarity	NPC475156
0.8667	High Similarity	NPC475633
0.866	High Similarity	NPC26413
0.866	High Similarity	NPC9613
0.866	High Similarity	NPC247139
0.866	High Similarity	NPC187933
0.8646	High Similarity	NPC32118
0.8646	High Similarity	NPC279974
0.8641	High Similarity	NPC274507
0.8632	High Similarity	NPC474806
0.8632	High Similarity	NPC275809
0.8632	High Similarity	NPC298554
0.8632	High Similarity	NPC118490
0.8632	High Similarity	NPC133579
0.8627	High Similarity	NPC275539

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 NPC260149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1699
0.2-0.3	3745
0.3-0.4	2273
0.4-0.5	745
0.5-0.6	247
0.6-0.7	173
0.7-0.8	62
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD7748	Approved
0.8854	High Similarity	NPD7902	Approved
0.8723	High Similarity	NPD7515	Phase 2
0.8542	High Similarity	NPD7901	Clinical (unspecified phase)
0.8542	High Similarity	NPD7900	Approved
0.8144	Intermediate Similarity	NPD8034	Phase 2
0.8144	Intermediate Similarity	NPD8035	Phase 2
0.8061	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5739	Approved
0.7905	Intermediate Similarity	NPD6675	Approved
0.7905	Intermediate Similarity	NPD6402	Approved
0.7905	Intermediate Similarity	NPD7128	Approved
0.7895	Intermediate Similarity	NPD8328	Phase 3
0.7895	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD7645	Phase 2
0.7778	Intermediate Similarity	NPD6411	Approved
0.7767	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7639	Approved
0.7757	Intermediate Similarity	NPD6899	Approved
0.7757	Intermediate Similarity	NPD7320	Approved
0.7757	Intermediate Similarity	NPD6881	Approved
0.7755	Intermediate Similarity	NPD5328	Approved
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7685	Intermediate Similarity	NPD6373	Approved
0.7685	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6372	Approved
0.7664	Intermediate Similarity	NPD5697	Approved
0.7664	Intermediate Similarity	NPD5701	Approved
0.7636	Intermediate Similarity	NPD8297	Approved
0.7615	Intermediate Similarity	NPD6883	Approved
0.7615	Intermediate Similarity	NPD7290	Approved
0.7615	Intermediate Similarity	NPD7102	Approved
0.7604	Intermediate Similarity	NPD4786	Approved
0.76	Intermediate Similarity	NPD6079	Approved
0.7593	Intermediate Similarity	NPD6011	Approved
0.7579	Intermediate Similarity	NPD3667	Approved
0.7576	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6101	Approved
0.757	Intermediate Similarity	NPD6008	Approved
0.7551	Intermediate Similarity	NPD3573	Approved
0.7545	Intermediate Similarity	NPD6617	Approved
0.7545	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6650	Approved
0.7545	Intermediate Similarity	NPD6869	Approved
0.7545	Intermediate Similarity	NPD6649	Approved
0.7545	Intermediate Similarity	NPD6847	Approved
0.7525	Intermediate Similarity	NPD5778	Approved
0.7525	Intermediate Similarity	NPD5779	Approved
0.7523	Intermediate Similarity	NPD6012	Approved
0.7523	Intermediate Similarity	NPD6013	Approved
0.7523	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6882	Approved
0.7475	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD3618	Phase 1
0.7411	Intermediate Similarity	NPD4632	Approved
0.7404	Intermediate Similarity	NPD4755	Approved
0.74	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7736	Approved
0.7308	Intermediate Similarity	NPD5222	Approved
0.7308	Intermediate Similarity	NPD4697	Phase 3
0.7308	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD7146	Approved
0.7273	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD7521	Approved
0.7273	Intermediate Similarity	NPD6409	Approved
0.7273	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD5330	Approved
0.7264	Intermediate Similarity	NPD4696	Approved
0.7264	Intermediate Similarity	NPD5286	Approved
0.7264	Intermediate Similarity	NPD5285	Approved
0.7264	Intermediate Similarity	NPD4700	Approved
0.7238	Intermediate Similarity	NPD5173	Approved
0.7238	Intermediate Similarity	NPD6083	Phase 2
0.7238	Intermediate Similarity	NPD6084	Phase 2
0.7217	Intermediate Similarity	NPD6009	Approved
0.7196	Intermediate Similarity	NPD5223	Approved
0.7188	Intermediate Similarity	NPD7525	Registered
0.7184	Intermediate Similarity	NPD4202	Approved
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7179	Intermediate Similarity	NPD6319	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7158	Intermediate Similarity	NPD6697	Approved
0.7158	Intermediate Similarity	NPD6118	Approved
0.7158	Intermediate Similarity	NPD6115	Approved
0.7158	Intermediate Similarity	NPD6114	Approved
0.7155	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.713	Intermediate Similarity	NPD5225	Approved
0.713	Intermediate Similarity	NPD4633	Approved
0.713	Intermediate Similarity	NPD5226	Approved
0.713	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.713	Intermediate Similarity	NPD6274	Approved
0.713	Intermediate Similarity	NPD5211	Phase 2
0.713	Intermediate Similarity	NPD5224	Approved
0.7129	Intermediate Similarity	NPD5737	Approved
0.7129	Intermediate Similarity	NPD6672	Approved
0.7129	Intermediate Similarity	NPD6903	Approved
0.7119	Intermediate Similarity	NPD5983	Phase 2
0.7117	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8293	Discontinued
0.7105	Intermediate Similarity	NPD8133	Approved
0.7094	Intermediate Similarity	NPD7101	Approved
0.7094	Intermediate Similarity	NPD7100	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.7071	Intermediate Similarity	NPD3665	Phase 1
0.7071	Intermediate Similarity	NPD3666	Approved
0.7071	Intermediate Similarity	NPD3133	Approved
0.7071	Intermediate Similarity	NPD3668	Phase 3
0.7069	Intermediate Similarity	NPD6317	Approved
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7064	Intermediate Similarity	NPD5174	Approved
0.7064	Intermediate Similarity	NPD4754	Approved
0.7064	Intermediate Similarity	NPD5175	Approved
0.7054	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6116	Phase 1
0.7034	Intermediate Similarity	NPD6054	Approved
0.7034	Intermediate Similarity	NPD6059	Approved
0.7025	Intermediate Similarity	NPD6336	Discontinued
0.7025	Intermediate Similarity	NPD6616	Approved
0.7009	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD6313	Approved
0.7	Intermediate Similarity	NPD5141	Approved
0.6992	Remote Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD4634	Approved
0.6981	Remote Similarity	NPD7732	Phase 3
0.6981	Remote Similarity	NPD7614	Phase 1
0.6975	Remote Similarity	NPD6909	Approved
0.6975	Remote Similarity	NPD6908	Approved
0.6967	Remote Similarity	NPD7078	Approved
0.6964	Remote Similarity	NPD6686	Approved
0.6947	Remote Similarity	NPD6117	Approved
0.6937	Remote Similarity	NPD4768	Approved
0.6937	Remote Similarity	NPD4767	Approved
0.6917	Remote Similarity	NPD6370	Approved
0.6887	Remote Similarity	NPD5695	Phase 3
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6053	Discontinued
0.6852	Remote Similarity	NPD4225	Approved
0.6852	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD6942	Approved
0.6842	Remote Similarity	NPD7339	Approved
0.6842	Remote Similarity	NPD3703	Phase 2
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4695	Discontinued
0.6833	Remote Similarity	NPD8515	Approved
0.6833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6015	Approved
0.6833	Remote Similarity	NPD8517	Approved
0.6833	Remote Similarity	NPD6016	Approved
0.6833	Remote Similarity	NPD8033	Approved
0.6833	Remote Similarity	NPD8513	Phase 3
0.6833	Remote Similarity	NPD8516	Approved
0.6814	Remote Similarity	NPD4730	Approved
0.6814	Remote Similarity	NPD5128	Approved
0.6814	Remote Similarity	NPD4729	Approved
0.6777	Remote Similarity	NPD5988	Approved
0.6771	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6098	Approved
0.6762	Remote Similarity	NPD7983	Approved
0.6762	Remote Similarity	NPD7637	Suspended
0.675	Remote Similarity	NPD8294	Approved
0.675	Remote Similarity	NPD8377	Approved
0.6737	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4753	Phase 2
0.6731	Remote Similarity	NPD6904	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6731	Remote Similarity	NPD6080	Approved
0.67	Remote Similarity	NPD6435	Approved
0.67	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5251	Approved
0.6696	Remote Similarity	NPD5248	Approved
0.6696	Remote Similarity	NPD5249	Phase 3
0.6696	Remote Similarity	NPD5247	Approved
0.6696	Remote Similarity	NPD5250	Approved
0.6696	Remote Similarity	NPD5135	Approved
0.6696	Remote Similarity	NPD5169	Approved
0.6696	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD8380	Approved
0.6694	Remote Similarity	NPD8379	Approved
0.6694	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.664	Remote Similarity	NPD6033	Approved
0.6638	Remote Similarity	NPD5216	Approved
0.6638	Remote Similarity	NPD5217	Approved
0.6638	Remote Similarity	NPD5215	Approved
0.6638	Remote Similarity	NPD5127	Approved
0.6604	Remote Similarity	NPD5281	Approved
0.6604	Remote Similarity	NPD5284	Approved
0.6602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6422	Discontinued
0.6602	Remote Similarity	NPD5279	Phase 3
0.6585	Remote Similarity	NPD6067	Discontinued
0.6583	Remote Similarity	NPD7328	Approved
0.6583	Remote Similarity	NPD7327	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