NPASS Compound

Structure

CID69627 OpenBabel06191715402D 32 36 0 0 1 0 0 0 0 0999 V2000 1.8399 4.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4268 3.7777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 -2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0414 -2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3705 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5279 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 0.4865 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 -1.6852 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2131 -1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 30 1 1 0 0 0 22 29 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 30 1 0 0 0 0 24 32 2 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	6.399
LogD:	5.109
LogS:	-6.24
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	4.992
Fsp3:	0.9
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:	-4.949
MDCK Permeability:	7.229225502669578e-06
Pgp-inhibitor:	0.139
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	95.00598907470703%
Volume Distribution (VD):	0.969
Pgp-substrate:	4.087507247924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.352
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.59

ADMET: Excretion

Clearance (CL):	7.142
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.898
Carcinogencity:	0.244
Eye Corrosion:	0.883
Eye Irritation:	0.578
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC69627

Natural Product ID:	NPC69627
*Common Name:**	1-Oxo-3Beta-Hydroxyolean-18-Ene
IUPAC Name:	(3S,4aS,6aS,6aR,6bR,8aR,14aS,14bR)-3-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-3,4a,5,6,6a,7,8,9,10,13,14,14a-dodecahydro-2H-picen-1-one
Synonyms:
Standard InCHIKey:	PKZZYOJERITBAM-HBSCMMAFSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-25(2)13-14-27(5)15-16-28(6)19(20(27)18-25)9-10-22-29(28,7)12-11-21-26(3,4)23(31)17-24(32)30(21,22)8/h18-19,21-23,31H,9-17H2,1-8H3/t19-,21+,22+,23+,27-,28-,29-,30+/m1/s1
SMILES:	O[C@H]1CC(=O)[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1(C2=CC(C)(C)CC1)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773213
PubChem CID:	52950910
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
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21309591]
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	twig	n.a.	PMID[21309591]
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO26307	Viburnum ayavacense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6515	Juglans sinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4636	Onopordum anatolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3731	Salix japonica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5560	Castor fiber	Species	Castoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26573	Artemisia umbelliformis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28	Cutleria multifida	Species	Cutleriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO941	Tiliacora triandra	Species	Menispermaceae	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
Others	9

Activity Type	# Activity
NON-MOLECULAR	1
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.2	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	1.9	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	53.2	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	14.0	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	17.8	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	5.0	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	43.6	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	10.6	%	PMID[544019]
NPT610	Others	Molecular identity unknown		Activity	=	18.8	%	PMID[544019]

☑ 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 NPC69627 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	204
0.1-0.2	1489
0.2-0.3	5487
0.3-0.4	13704
0.4-0.5	10117
0.5-0.6	5241
0.6-0.7	4242
0.7-0.8	1760
0.8-0.85	202
0.85-0.9	186
0.9-0.95	61
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.954	High Similarity	NPC474529
0.9518	High Similarity	NPC133954
0.9405	High Similarity	NPC74363
0.9405	High Similarity	NPC475862
0.9405	High Similarity	NPC213412
0.9294	High Similarity	NPC73064
0.9195	High Similarity	NPC86372
0.9195	High Similarity	NPC172361
0.9176	High Similarity	NPC95594
0.9176	High Similarity	NPC477579
0.9176	High Similarity	NPC235341
0.9167	High Similarity	NPC180834
0.9091	High Similarity	NPC155120
0.9091	High Similarity	NPC324341
0.9091	High Similarity	NPC966
0.9091	High Similarity	NPC6255
0.9091	High Similarity	NPC471588
0.9091	High Similarity	NPC228784
0.9091	High Similarity	NPC282616
0.9091	High Similarity	NPC288833
0.907	High Similarity	NPC98442
0.907	High Similarity	NPC88716
0.907	High Similarity	NPC102683
0.907	High Similarity	NPC130577
0.907	High Similarity	NPC307426
0.907	High Similarity	NPC171203
0.907	High Similarity	NPC51700
0.907	High Similarity	NPC142415
0.907	High Similarity	NPC68160
0.907	High Similarity	NPC242468
0.907	High Similarity	NPC18064
0.907	High Similarity	NPC293564
0.9036	High Similarity	NPC3915
0.9	High Similarity	NPC148523
0.9	High Similarity	NPC139570
0.8989	High Similarity	NPC298554
0.8977	High Similarity	NPC291028
0.8966	High Similarity	NPC17733
0.8966	High Similarity	NPC40552
0.8966	High Similarity	NPC474512
0.8966	High Similarity	NPC52169
0.8966	High Similarity	NPC181225
0.8966	High Similarity	NPC246708
0.8966	High Similarity	NPC470629
0.8966	High Similarity	NPC290690
0.8966	High Similarity	NPC473242
0.8966	High Similarity	NPC182797
0.8953	High Similarity	NPC72638
0.8929	High Similarity	NPC310989
0.8929	High Similarity	NPC163236
0.8901	High Similarity	NPC98874
0.8889	High Similarity	NPC209868
0.8889	High Similarity	NPC222047
0.8876	High Similarity	NPC233455
0.8876	High Similarity	NPC474525
0.8876	High Similarity	NPC4036
0.8876	High Similarity	NPC145067
0.8876	High Similarity	NPC65120
0.8876	High Similarity	NPC105189
0.8876	High Similarity	NPC158030
0.8864	High Similarity	NPC274330
0.8864	High Similarity	NPC474972
0.8864	High Similarity	NPC121798
0.8864	High Similarity	NPC234346
0.8864	High Similarity	NPC161751
0.8864	High Similarity	NPC130520
0.8864	High Similarity	NPC293048
0.8864	High Similarity	NPC127689
0.8864	High Similarity	NPC290972
0.8864	High Similarity	NPC470588
0.8864	High Similarity	NPC95246
0.8864	High Similarity	NPC59263
0.8864	High Similarity	NPC61543
0.8864	High Similarity	NPC25906
0.8864	High Similarity	NPC64872
0.8864	High Similarity	NPC143232
0.8864	High Similarity	NPC225585
0.8864	High Similarity	NPC263393
0.8864	High Similarity	NPC270768
0.8864	High Similarity	NPC198664
0.8851	High Similarity	NPC158141
0.8851	High Similarity	NPC298904
0.8851	High Similarity	NPC57469
0.8851	High Similarity	NPC173089
0.8837	High Similarity	NPC274724
0.8791	High Similarity	NPC473240
0.8778	High Similarity	NPC272075
0.8778	High Similarity	NPC295643
0.8778	High Similarity	NPC214756
0.8764	High Similarity	NPC227467
0.8764	High Similarity	NPC290614
0.8764	High Similarity	NPC46441
0.8764	High Similarity	NPC273621
0.8764	High Similarity	NPC126369
0.8764	High Similarity	NPC210037
0.8764	High Similarity	NPC120968
0.8764	High Similarity	NPC7260
0.8764	High Similarity	NPC18872
0.8764	High Similarity	NPC477872
0.8764	High Similarity	NPC470589
0.8764	High Similarity	NPC111110
0.8764	High Similarity	NPC193750
0.8764	High Similarity	NPC130278
0.875	High Similarity	NPC474511
0.875	High Similarity	NPC53911
0.875	High Similarity	NPC474925
0.875	High Similarity	NPC472802
0.875	High Similarity	NPC1753
0.8736	High Similarity	NPC158393
0.8721	High Similarity	NPC227132
0.8706	High Similarity	NPC48362
0.8696	High Similarity	NPC201657
0.8696	High Similarity	NPC132824
0.8696	High Similarity	NPC476327
0.8696	High Similarity	NPC476318
0.8681	High Similarity	NPC471207
0.8681	High Similarity	NPC78580
0.8681	High Similarity	NPC184006
0.8681	High Similarity	NPC23621
0.8681	High Similarity	NPC148964
0.8667	High Similarity	NPC235884
0.8667	High Similarity	NPC71074
0.8667	High Similarity	NPC38754
0.8667	High Similarity	NPC187722
0.8667	High Similarity	NPC472149
0.8667	High Similarity	NPC300351
0.8667	High Similarity	NPC25299
0.8667	High Similarity	NPC306541
0.8667	High Similarity	NPC52021
0.8667	High Similarity	NPC84319
0.8652	High Similarity	NPC474686
0.8646	High Similarity	NPC474281
0.8646	High Similarity	NPC284865
0.8636	High Similarity	NPC71507
0.8602	High Similarity	NPC106112
0.8602	High Similarity	NPC189880
0.8602	High Similarity	NPC26413
0.8602	High Similarity	NPC187933
0.8602	High Similarity	NPC261935
0.8588	High Similarity	NPC14151
0.8587	High Similarity	NPC23241
0.8587	High Similarity	NPC195715
0.8571	High Similarity	NPC63118
0.8571	High Similarity	NPC136313
0.8571	High Similarity	NPC118490
0.8571	High Similarity	NPC202728
0.8571	High Similarity	NPC307335
0.8571	High Similarity	NPC118519
0.8571	High Similarity	NPC275809
0.8571	High Similarity	NPC158059
0.8571	High Similarity	NPC74855
0.8571	High Similarity	NPC86368
0.8571	High Similarity	NPC49776
0.8571	High Similarity	NPC474436
0.8571	High Similarity	NPC229281
0.8556	High Similarity	NPC113989
0.8556	High Similarity	NPC474728
0.8556	High Similarity	NPC120840
0.8556	High Similarity	NPC85173
0.8556	High Similarity	NPC49320
0.8554	High Similarity	NPC34177
0.8554	High Similarity	NPC101475
0.8554	High Similarity	NPC157996
0.8554	High Similarity	NPC40394
0.8539	High Similarity	NPC206060
0.8539	High Similarity	NPC328539
0.8539	High Similarity	NPC230387
0.8523	High Similarity	NPC470955
0.8511	High Similarity	NPC111214
0.8511	High Similarity	NPC174663
0.8511	High Similarity	NPC188833
0.8511	High Similarity	NPC260149
0.8511	High Similarity	NPC271614
0.8511	High Similarity	NPC29765
0.8511	High Similarity	NPC58942
0.8511	High Similarity	NPC164349
0.8506	High Similarity	NPC171789
0.8495	Intermediate Similarity	NPC472806
0.8495	Intermediate Similarity	NPC157113
0.8495	Intermediate Similarity	NPC167193
0.8495	Intermediate Similarity	NPC5532
0.8495	Intermediate Similarity	NPC62516
0.8495	Intermediate Similarity	NPC61369
0.8495	Intermediate Similarity	NPC469545
0.8478	Intermediate Similarity	NPC231063
0.8478	Intermediate Similarity	NPC145667
0.8478	Intermediate Similarity	NPC282395
0.8478	Intermediate Similarity	NPC114159
0.8478	Intermediate Similarity	NPC23170
0.8478	Intermediate Similarity	NPC32407
0.8478	Intermediate Similarity	NPC159365
0.8478	Intermediate Similarity	NPC74751
0.8478	Intermediate Similarity	NPC263548
0.8478	Intermediate Similarity	NPC191412
0.8478	Intermediate Similarity	NPC6818
0.8478	Intermediate Similarity	NPC299996
0.8478	Intermediate Similarity	NPC20235
0.8478	Intermediate Similarity	NPC88116
0.8478	Intermediate Similarity	NPC91010
0.8462	Intermediate Similarity	NPC285184

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 NPC69627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1850
0.2-0.3	4028
0.3-0.4	2088
0.4-0.5	596
0.5-0.6	167
0.6-0.7	178
0.7-0.8	48
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8876	High Similarity	NPD7515	Phase 2
0.8652	High Similarity	NPD5328	Approved
0.8478	Intermediate Similarity	NPD7748	Approved
0.8462	Intermediate Similarity	NPD6079	Approved
0.8353	Intermediate Similarity	NPD7645	Phase 2
0.8315	Intermediate Similarity	NPD3618	Phase 1
0.8295	Intermediate Similarity	NPD4786	Approved
0.8276	Intermediate Similarity	NPD3667	Approved
0.8211	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4697	Phase 3
0.7917	Intermediate Similarity	NPD5221	Approved
0.7917	Intermediate Similarity	NPD5222	Approved
0.7895	Intermediate Similarity	NPD7900	Approved
0.7895	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3666	Approved
0.7889	Intermediate Similarity	NPD3665	Phase 1
0.7889	Intermediate Similarity	NPD3133	Approved
0.7835	Intermediate Similarity	NPD5173	Approved
0.7835	Intermediate Similarity	NPD4755	Approved
0.7789	Intermediate Similarity	NPD4202	Approved
0.7677	Intermediate Similarity	NPD5286	Approved
0.7677	Intermediate Similarity	NPD4700	Approved
0.7677	Intermediate Similarity	NPD4696	Approved
0.7677	Intermediate Similarity	NPD5285	Approved
0.76	Intermediate Similarity	NPD5223	Approved
0.7527	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5224	Approved
0.7525	Intermediate Similarity	NPD5211	Phase 2
0.7525	Intermediate Similarity	NPD5225	Approved
0.7525	Intermediate Similarity	NPD5226	Approved
0.7525	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD6411	Approved
0.7476	Intermediate Similarity	NPD5739	Approved
0.7476	Intermediate Similarity	NPD6675	Approved
0.7476	Intermediate Similarity	NPD7128	Approved
0.7476	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD5175	Approved
0.7451	Intermediate Similarity	NPD5174	Approved
0.7451	Intermediate Similarity	NPD4754	Approved
0.7447	Intermediate Similarity	NPD3573	Approved
0.7444	Intermediate Similarity	NPD7525	Registered
0.7423	Intermediate Similarity	NPD6399	Phase 3
0.7379	Intermediate Similarity	NPD5141	Approved
0.7368	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4634	Approved
0.7345	Intermediate Similarity	NPD8328	Phase 3
0.734	Intermediate Similarity	NPD5279	Phase 3
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.732	Intermediate Similarity	NPD8035	Phase 2
0.732	Intermediate Similarity	NPD8034	Phase 2
0.7308	Intermediate Similarity	NPD4767	Approved
0.7308	Intermediate Similarity	NPD4768	Approved
0.7292	Intermediate Similarity	NPD6101	Approved
0.7292	Intermediate Similarity	NPD4753	Phase 2
0.7292	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4221	Approved
0.7283	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD3703	Phase 2
0.7273	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7264	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD6373	Approved
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7238	Intermediate Similarity	NPD5701	Approved
0.7238	Intermediate Similarity	NPD5697	Approved
0.7234	Intermediate Similarity	NPD5329	Approved
0.7204	Intermediate Similarity	NPD4788	Approved
0.7196	Intermediate Similarity	NPD7290	Approved
0.7196	Intermediate Similarity	NPD7102	Approved
0.7196	Intermediate Similarity	NPD6883	Approved
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5128	Approved
0.717	Intermediate Similarity	NPD4730	Approved
0.717	Intermediate Similarity	NPD6011	Approved
0.717	Intermediate Similarity	NPD4729	Approved
0.717	Intermediate Similarity	NPD5168	Approved
0.7158	Intermediate Similarity	NPD7146	Approved
0.7158	Intermediate Similarity	NPD7521	Approved
0.7158	Intermediate Similarity	NPD7334	Approved
0.7158	Intermediate Similarity	NPD6409	Approved
0.7158	Intermediate Similarity	NPD6684	Approved
0.7158	Intermediate Similarity	NPD5330	Approved
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6847	Approved
0.7128	Intermediate Similarity	NPD4197	Approved
0.7126	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6013	Approved
0.7103	Intermediate Similarity	NPD6014	Approved
0.7103	Intermediate Similarity	NPD6012	Approved
0.7093	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8297	Approved
0.7064	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD5247	Approved
0.7037	Intermediate Similarity	NPD5135	Approved
0.7037	Intermediate Similarity	NPD5248	Approved
0.7037	Intermediate Similarity	NPD5250	Approved
0.7037	Intermediate Similarity	NPD5249	Phase 3
0.7037	Intermediate Similarity	NPD5251	Approved
0.7037	Intermediate Similarity	NPD5169	Approved
0.7037	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3617	Approved
0.703	Intermediate Similarity	NPD7614	Phase 1
0.701	Intermediate Similarity	NPD6903	Approved
0.699	Remote Similarity	NPD7639	Approved
0.699	Remote Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD4623	Approved
0.6979	Remote Similarity	NPD5205	Approved
0.6979	Remote Similarity	NPD4690	Approved
0.6979	Remote Similarity	NPD4519	Discontinued
0.6979	Remote Similarity	NPD4689	Approved
0.6979	Remote Similarity	NPD4688	Approved
0.6979	Remote Similarity	NPD4138	Approved
0.6979	Remote Similarity	NPD4693	Phase 3
0.6972	Remote Similarity	NPD5217	Approved
0.6972	Remote Similarity	NPD5127	Approved
0.6972	Remote Similarity	NPD5215	Approved
0.6972	Remote Similarity	NPD5216	Approved
0.6964	Remote Similarity	NPD7115	Discovery
0.6961	Remote Similarity	NPD6084	Phase 2
0.6961	Remote Similarity	NPD6083	Phase 2
0.6931	Remote Similarity	NPD4629	Approved
0.6931	Remote Similarity	NPD5210	Approved
0.693	Remote Similarity	NPD6054	Approved
0.693	Remote Similarity	NPD6059	Approved
0.69	Remote Similarity	NPD5779	Approved
0.69	Remote Similarity	NPD5778	Approved
0.6875	Remote Similarity	NPD6868	Approved
0.6847	Remote Similarity	NPD4632	Approved
0.6837	Remote Similarity	NPD5737	Approved
0.6837	Remote Similarity	NPD6672	Approved
0.6818	Remote Similarity	NPD4244	Approved
0.6818	Remote Similarity	NPD4245	Approved
0.6813	Remote Similarity	NPD6117	Approved
0.681	Remote Similarity	NPD6370	Approved
0.6807	Remote Similarity	NPD7736	Approved
0.6804	Remote Similarity	NPD5690	Phase 2
0.6804	Remote Similarity	NPD4694	Approved
0.6804	Remote Similarity	NPD5280	Approved
0.6789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5167	Approved
0.6783	Remote Similarity	NPD6319	Approved
0.6778	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD6335	Approved
0.6744	Remote Similarity	NPD7331	Phase 2
0.6739	Remote Similarity	NPD6116	Phase 1
0.6726	Remote Similarity	NPD6274	Approved
0.6724	Remote Similarity	NPD6015	Approved
0.6724	Remote Similarity	NPD6016	Approved
0.6705	Remote Similarity	NPD3698	Phase 2
0.6705	Remote Similarity	NPD4137	Phase 3
0.6702	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7732	Phase 3
0.6697	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6695	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6639	Remote Similarity	NPD6616	Approved
0.6633	Remote Similarity	NPD6098	Approved
0.6632	Remote Similarity	NPD4139	Approved
0.6632	Remote Similarity	NPD4692	Approved
0.6629	Remote Similarity	NPD4691	Approved
0.6629	Remote Similarity	NPD4789	Approved
0.6629	Remote Similarity	NPD4747	Approved
0.6628	Remote Similarity	NPD7341	Phase 2
0.6609	Remote Similarity	NPD6313	Approved
0.6609	Remote Similarity	NPD6314	Approved
0.6602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5695	Phase 3
0.6596	Remote Similarity	NPD4195	Approved
0.6593	Remote Similarity	NPD6926	Approved
0.6593	Remote Similarity	NPD6924	Approved
0.6591	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5360	Phase 3
0.6583	Remote Similarity	NPD8293	Discontinued
0.6583	Remote Similarity	NPD7078	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